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Georg Thieme Verlag KGerschienen am01.07.2014
The Science of Synthesis Editorial Board,together with the volume editors and authors, is constantly reviewing the whole field of synthetic organic chemistry as presented in Science of Synthesis and evaluating significant developments in synthetic methodology. Four annual volumes updating content across all categories ensure that you always have access to state-of-the-art synthetic methodology.

Content of this volume:
Germanium cyanides, acylgermanes, a-halo- and a-alkoxyvinylgermanes, a-halo-, a-hydroxy-, a-alkoxy-, and a-aminoalkylgermanes, alkynylgermanes, aryl- and heteroarylgermanes, propargyl- and allenylgermanes, selenophenes,
tellurophenes, isoxazoles, 1,2-benzisoxazoles and related compounds, benzoxazoles and other annulated oxazoles, isothiazoles, benzisothiazoles, benzothiazoles, isoselenazoles, annulated isoselenazole compounds, selenazoles, annulated selenazole compounds, isotellurazoles, and annulated isotellurazole and tellurazole compounds, pyridopyrazines and iodoarenes.mehr
Verfügbare Formate
BuchGebunden
EUR2.589,99
EUR2.589,99

Produkt

KlappentextThe Science of Synthesis Editorial Board,together with the volume editors and authors, is constantly reviewing the whole field of synthetic organic chemistry as presented in Science of Synthesis and evaluating significant developments in synthetic methodology. Four annual volumes updating content across all categories ensure that you always have access to state-of-the-art synthetic methodology.

Content of this volume:
Germanium cyanides, acylgermanes, a-halo- and a-alkoxyvinylgermanes, a-halo-, a-hydroxy-, a-alkoxy-, and a-aminoalkylgermanes, alkynylgermanes, aryl- and heteroarylgermanes, propargyl- and allenylgermanes, selenophenes,
tellurophenes, isoxazoles, 1,2-benzisoxazoles and related compounds, benzoxazoles and other annulated oxazoles, isothiazoles, benzisothiazoles, benzothiazoles, isoselenazoles, annulated isoselenazole compounds, selenazoles, annulated selenazole compounds, isotellurazoles, and annulated isotellurazole and tellurazole compounds, pyridopyrazines and iodoarenes.
Details
Weitere ISBN/GTIN9783131786319
ProduktartE-Book
EinbandartE-Book
FormatEPUB
Erscheinungsjahr2014
Erscheinungsdatum01.07.2014
Seiten580 Seiten
SpracheEnglisch
Dateigrösse17238
Artikel-Nr.1478014
Rubriken
Genre9200

Inhalt/Kritik

Inhaltsverzeichnis
1;Science of Synthesis: Knowledge Updates 2010/1;1
1.1;Title page;5
1.2;Imprint;7
1.3;Preface;8
1.4;Abstracts;10
1.5;Overview;24
1.6;Table of Contents;26
1.7;Volume 5: Compounds of Group 14 (Ge, Sn, Pb);48
1.7.1;5.1 Product Class 1: Germanium Compounds;48
1.7.1.1;5.1.1.8 Germanium Hydrides;48
1.7.1.1.1;5.1.1.8.1 Method 1: Synthesis by Reduction of Germanium Halides;49
1.7.1.1.2;5.1.1.8.2 Method 2: Applications in Reduction of Organic Halides;49
1.7.1.1.3;5.1.1.8.3 Method 3: Applications in Hydrogermylation of C--C Multiple Bonds;50
1.7.1.1.4;5.1.1.8.4 Method 4: Applications with Acids and Bases;51
1.7.1.1.5;5.1.1.8.5 Method 5: Applications in Palladium(0)-Catalyzed Coupling Reactions;52
1.7.1.1.6;5.1.1.8.6 Method 6: Application as an Alternative to Tributyltin Hydride in Radical Chain Reactions;54
1.7.1.1.7;5.1.1.8.7 Method 7: Application as Precursors for Germyl Cation Generation;55
1.7.1.2;5.1.15.2 Germanium Cyanides;58
1.7.1.2.1;5.1.15.2.1 Method 1: Synthesis from Halogermanes by Substitution with Trialkylsilyl Cyanides;58
1.7.1.3;5.1.16.6 Acylgermanes;62
1.7.1.3.1;5.1.16.6.1 Method 1: Synthesis from Germyl Enol Ethers by Hydrolysis;62
1.7.1.3.2;5.1.16.6.2 Method 2: Synthesis from a,a-Diheterosubstituted Germanes by Hydrolysis;63
1.7.1.3.3;5.1.16.6.3 Method 3: Synthesis from Terminal Alkynes by Carbonylation;64
1.7.1.3.4;5.1.16.6.4 Method 4: Application of Acylgermanes as Radical Acceptors;65
1.7.1.3.5;5.1.16.6.5 Method 5: Application of Acylgermanes as Amide Precursors;66
1.7.1.4;5.1.18.4 a-Halo-and a-Alkoxyvinylgermanes;68
1.7.1.4.1;5.1.18.4.1 Method 1: Synthesis of a-Alkoxyvinylgermanes from a-Metallovinyl Ethers by Substitution;68
1.7.1.4.2;5.1.18.4.2 Method 2: Synthesis of a-Halovinylgermanes from Alk-1-ynylgermanes by Hydro/Carbometalation-Halogenation;69
1.7.1.4.3;5.1.18.4.3 Method 3: Synthesis of a-Halovinylgermanes from a-Halovinyl Sulfones by Radical-Mediated Desulfonylation;71
1.7.1.4.4;5.1.18.4.4 Method 4: Application of a-Halovinylgermanes in Palladium-Catalyzed Cross Coupling with Organic Halides;72
1.7.1.5;5.1.19.7 a-Halo-, a-Hydroxy,- a-Alkoxy-, and a-Aminoalkylgermanes;74
1.7.1.5.1;5.1.19.7.1 Method 1: Synthesis of a-Hetero- and a-Haloalkylgermanes from Halogermanes by Substitution;75
1.7.1.5.2;5.1.19.7.2 Method 2: Synthesis by Interconversion of a-Hetero- and a-Haloalkylgermanes by Substitution;76
1.7.1.5.3;5.1.19.7.3 Method 3: Synthesis of a-Hydroxyalkylgermanes from Hydroboration of Vinylgermanes;76
1.7.1.5.4;5.1.19.7.4 Method 4: Synthesis of a-Aminoalkylgermanes by [3 + 2] Cycloaddition of Germenes to Imino Esters;77
1.7.1.5.5;5.1.19.7.5 Method 5: Application of Lithiated a-Haloalkylgermanes in gem-Silylation/Borylation Reactions To Give Polymetalated Methanes;78
1.7.1.6;5.1.20.4 Alkynylgermanes;82
1.7.1.6.1;5.1.20.4.1 Method 1: Synthesis from Halogermanes by Substitution;83
1.7.1.6.2;5.1.20.4.2 Method 2: Synthesis from Group 14 Metalloalkynyls by Metathesis with Alkenylgermanes;83
1.7.1.6.3;5.1.20.4.3 Method 3: Synthesis by Substitution with Aminogermanes;84
1.7.1.6.4;5.1.20.4.4 Method 4: Synthesis by Elimination of a-Alkoxyalkenylgermanes;84
1.7.1.6.5;5.1.20.4.5 Method 5: Applications of Alkynylgermanes as Protecting Groups;85
1.7.1.6.6;5.1.20.4.6 Method 6: Applications of Alkynylgermanes in Palladium(0)-Catalyzed Cross-Coupling Reactions;86
1.7.1.7;5.1.22.6 Aryl- and Heteroarylgermanes;88
1.7.1.7.1;5.1.22.6.1 Method 1: Synthesis from Halogermanes by Substitution with Arylmetals;88
1.7.1.7.1.1;5.1.22.6.1.1 Variation 1: Using Preformed Arylmetals;88
1.7.1.7.1.2;5.1.22.6.1.2 Variation 2: Using Barbier-Type Reactions;88
1.7.1.7.2;5.1.22.6.2 Method 2: Synthesis from Aryl Halides by Palladium(0)-Mediated Coupling with Germanium Hydrides;89
1.7.1.7.3;5.1.22.6.3 Method 3: Synthesis from Arylstannanes by Transmetalation with Germanium(IV) Chloride;89
1.7.1.7.4;5.1.22.6.4 Method 4: Synthesis of Aryl- and Heteroarylgermanes by Cycloaddition;90
1.7.1.7.5;5.1.22.6.5 Method 5: Applications of Arylgermanes as Linkers for Solid-Phase Synthesis;91
1.7.1.7.6;5.1.22.6.6 Method 6: Applications of Arylgermanes in Palladium(0)-Catalyzed Cross-Coupling Reactions;91
1.7.1.8;5.1.23.6 Vinylgermanes;96
1.7.1.8.1;5.1.23.6.1 Method 1: Synthesis from Vinyllithium and Vinyl Grignard Reagents by Transmetalation with Halogermanes;96
1.7.1.8.2;5.1.23.6.2 Method 2: Synthesis from Alkynes by Hydro-, Hetero-, and Metallogermylation;97
1.7.1.8.2.1;5.1.23.6.2.1 Variation 1: By Hydrogermylation;97
1.7.1.8.2.2;5.1.23.6.2.2 Variation 2: By Palladium(0)-Mediated Germylation;98
1.7.1.8.2.3;5.1.23.6.2.3 Variation 3: By Metallogermylation;99
1.7.1.8.3;5.1.23.6.3 Method 3: Synthesis from Vinylgermanes by Ruthenium-Catalyzed Metathesis;100
1.7.1.8.4;5.1.23.6.4 Method 4: Applications in Palladium(0)-Catalyzed Cross Coupling of Organic Halides;101
1.7.1.9;5.1.24.4 Propargyl- and Allenylgermanes;106
1.7.1.9.1;5.1.24.4.1 Method 1: Synthesis of Propargyl- and Allenylgermanes by Substitution;106
1.7.1.9.2;5.1.24.4.2 Method 2: Application of Allenylgermanes in [2 + 2]-Cycloaddition Reactions with Imino Esters;107
1.7.1.10;5.1.25.3 Benzylgermanes;110
1.7.1.10.1;5.1.25.3.1 Method 1: Synthesis from Halogermanes by Substitution with Benzylmetals;111
1.7.1.10.2;5.1.25.3.2 Method 2: Application in Palladium(0)-Catalyzed Cross Coupling;112
1.7.1.11;5.1.26.6 Allylgermanes;116
1.7.1.11.1;5.1.26.6.1 Method 1: Synthesis from Halogermanes by Substitution with Allylmetals;117
1.7.1.11.2;5.1.26.6.2 Method 2: Synthesis from Allyl Halides or Dienes by Germylene Insertion;118
1.7.1.11.3;5.1.26.6.3 Method 3: Synthesis from Allyl Halides by Palladium(0)-Mediated Coupling with Metallogermanes;118
1.7.1.11.4;5.1.26.6.4 Method 4: Synthesis from 3,4-Epoxypent-1-enes by Germyl Radical Addition;120
1.7.1.12;5.1.27.4 Alkylgermanes;124
1.7.1.12.1;5.1.27.4.1 Method 1: Synthesis from Halogermanes by Substitution with Alkylmetals;125
1.7.1.12.2;5.1.27.4.2 Method 2: Synthesis from Alkenes by Hydrogermylation;125
1.8;Volume 9:Fully Unsaturated Small Ring Heterocycles and Monocyclic Five-Membered Hetarenes with One Heteroatom;128
1.8.1;9.11 Product Class 11: Selenophenes;128
1.8.1.1;9.11.4 Selenophenes;128
1.8.1.1.1;9.11.4.1 Synthesis by Ring-Closure Reactions;128
1.8.1.1.1.1;9.11.4.1.1 By Formation of Two Se--C Bonds and One C--C Bond;128
1.8.1.1.1.1.1;9.11.4.1.1.1 Fragments C--C--C, C, and Se;128
1.8.1.1.1.1.1.1;9.11.4.1.1.1.1 Method 1: From Ketene Dithioacetals and Sodium Selenide;128
1.8.1.1.1.1.1.2;9.11.4.1.1.1.2 Method 2: From ß-Chloroacrylonitriles and Sodium Selenide;130
1.8.1.1.1.1.2;9.11.4.1.1.2 Fragments C--C, C--C, and Se;131
1.8.1.1.1.1.2.1;9.11.4.1.1.2.1 Method 1: From Diphosphorylacetylene and Sodium Hydroselenide;131
1.8.1.1.1.2;9.11.4.1.2 By Formation of Two Se--C Bonds;132
1.8.1.1.1.2.1;9.11.4.1.2.1 Fragments C--C--C--C and Se;132
1.8.1.1.1.2.1.1;9.11.4.1.2.1.1 Method 1: Reaction of C4 Building Blocks with Sources of Selenium;132
1.8.1.1.1.2.1.1.1;9.11.4.1.2.1.1.1 Variation 1: Reaction of Conjugated 1,3-Dienes with Selenium Dioxide;132
1.8.1.1.1.3;9.11.4.1.3 By Formation of One Se--C Bond;133
1.8.1.1.1.3.1;9.11.4.1.3.1 Fragment Se--C--C--C--C;133
1.8.1.1.1.3.1.1;9.11.4.1.3.1.1 Method 1: Electrophilic Cyclization of Z-Selanylenynes;133
1.8.1.1.1.3.1.1.1;9.11.4.1.3.1.1.1 Variation 1: Reaction with Butyltellurium Tribromide;133
1.8.1.1.1.3.1.1.2;9.11.4.1.3.1.1.2 Variation 2: Reaction with Other Electrophiles;133
1.8.1.1.1.3.1.1.3;9.11.4.1.3.1.1.3 Variation 3: Copper(I) Iodide Catalyzed Cyclization;135
1.8.1.1.1.4;9.11.4.1.4 By Formation of One C--C Bond;135
1.8.1.1.1.4.1;9.11.4.1.4.1 Fragment C--C--C--Se--C;135
1.8.1.1.1.4.1.1;9.11.4.1.4.1.1 Method 1: Cyclization of a Dipropargyl Selenide;135
1.8.1.1.2;9.11.4.2 Synthesis by Ring Transformation;136
1.8.1.1.2.1;9.11.4.2.1 Method 1: Thermal Decomposition of Selenadiazoles in the Presence of Arylacetylenes;136
1.8.1.1.2.2;9.11.4.2.2 Method 2: Formal Exchange of Magnesium with Selenium;137
1.8.1.1.3;9.11.4.3 Synthesis by Substituent Modification;138
1.8.1.1.3.1;9.11.4.3.1 Substitution of Metals;138
1.8.1.1.3.1.1;9.11.4.3.1.1 Method 1: Substitution Reactions Involving Organoboron Derivatives;138
1.8.1.1.3.2;9.11.4.3.2 Substitution of Heteroatoms;138
1.8.1.1.3.2.1;9.11.4.3.2.1 Method 1: Substitution of Halogens by Lithium;138
1.8.1.1.3.2.2;9.11.4.3.2.2 Method 2: Metal-Assisted Cross Coupling of Haloselenophenes;140
1.8.1.1.3.2.2.1;9.11.4.3.2.2.1 Variation 1: Coupling with Alkynes;140
1.8.1.1.3.2.2.2;9.11.4.3.2.2.2 Variation 2: Coupling with Alcohols;141
1.8.1.1.3.2.2.3;9.11.4.3.2.2.3 Variation 3: Coupling with Thiols;142
1.8.2;9.12 Product Class 12: Tellurophenes;146
1.8.2.1;9.12.3 Tellurophenes;146
1.8.2.1.1;9.12.3.1 Synthesis by Ring-Closure Reactions;147
1.8.2.1.1.1;9.12.3.1.1 By Formation of Two Te--C Bonds;147
1.8.2.1.1.1.1;9.12.3.1.1.1 Fragments C--C--C--C and Te;147
1.8.2.1.1.1.1.1;9.12.3.1.1.1.1 Method 1: Reaction of C4 Building Blocks with Sources of Tellurium;147
1.8.2.1.1.1.1.1.1;9.12.3.1.1.1.1.1 Variation 1: Reaction of 2,3-Dimethoxybuta-1,3-diene with Tellurium Dichloride;147
1.8.2.1.1.1.1.1.2;9.12.3.1.1.1.1.2 Variation 2: Reaction of In Situ Generated Sodium Telluride and Buta-1,3-diyne;147
1.8.2.1.1.1.1.1.3;9.12.3.1.1.1.1.3 Variation 3: Reaction of 1,4-Diphenylbuta-1,3-diyne with Diethyl Ditelluride;148
1.8.2.1.1.2;9.12.3.1.2 By Formation of One Te--C Bond;149
1.8.2.1.1.2.1;9.12.3.1.2.1 Fragment Te--C--C--C--C;149
1.8.2.1.1.2.1.1;9.12.3.1.2.1.1 Method 1: Cyclization of 1-(Alkyltellanyl)but-1-en-3-ynes;149
1.8.2.1.1.2.1.1.1;9.12.3.1.2.1.1.1 Variation 1: Reaction with Butyltellurium Tribromide;149
1.8.2.1.1.2.1.1.2;9.12.3.1.2.1.1.2 Variation 2: Reaction with a Copper(I) Iodide Catalyst;150
1.8.2.1.2;9.12.3.2 Synthesis by Substituent Modification;150
1.8.2.1.2.1;9.12.3.2.1 Substitution of Metals;150
1.8.2.1.2.1.1;9.12.3.2.1.1 Method 1: Substitution Reactions Involving Organostannanes;150
1.8.2.1.2.1.2;9.12.3.2.1.2 Method 2: Substitution Reactions Involving Organoboron Derivatives;152
1.8.2.1.2.2;9.12.3.2.2 Substitution of Heteroatoms;152
1.8.2.1.2.2.1;9.12.3.2.2.1 Method 1: Metal-Assisted Cross Coupling of Halotellurophenes with Alkynes;152
1.9;Volume 11: Five-Membered Hetarenes with One Chalcogen and One Additional Heteroatom;156
1.9.1;11.9 Product Class 9: Isoxazoles;156
1.9.1.1;11.9.5 Isoxazoles;156
1.9.1.1.1;11.9.5.1 Synthesis by Ring-Closure Reactions;156
1.9.1.1.1.1;11.9.5.1.1 By Formation of Two Heteroatom--Carbon Bonds and One C--C Bond;156
1.9.1.1.1.1.1;11.9.5.1.1.1 Fragments C--C, N--O, and C;156
1.9.1.1.1.1.1.1;11.9.5.1.1.1.1 Method 1: One-Pot Four-Component Coupling;156
1.9.1.1.1.2;11.9.5.1.2 By Formation of Two Heteroatom--Carbon Bonds;156
1.9.1.1.1.2.1;11.9.5.1.2.1 Fragments C--C--C and N--O;156
1.9.1.1.1.2.1.1;11.9.5.1.2.1.1 Method 1: Synthesis of Hydroxyisoxazoles and Isoxazolones by Reactions of Hydroxylamine with 3-Oxo Esters and 1,3-Diesters;157
1.9.1.1.1.2.1.2;11.9.5.1.2.1.2 Method 2: By Reactions of Hydroxylamine with a,ß-Unsaturated Carbonyl Compounds;158
1.9.1.1.1.3;11.9.5.1.3 By Formation of One Heteroatom--Carbon and One C--C Bond;159
1.9.1.1.1.3.1;11.9.5.1.3.1 Fragments O--N--C and C--C;159
1.9.1.1.1.3.1.1;11.9.5.1.3.1.1 Method 1: From Nitrile Oxides and Alkynes;159
1.9.1.1.1.3.1.1.1;11.9.5.1.3.1.1.1 Variation 1: Using Terminal Alkynes;159
1.9.1.1.1.3.1.1.2;11.9.5.1.3.1.1.2 Variation 2: Using Disubstituted Alkynes;164
1.9.1.1.1.3.1.2;11.9.5.1.3.1.2 Method 2: By Cycloaddition of Nitrile Oxides to C=C Bonds, Accompanied by Elimination or Dehydration;167
1.9.1.1.1.3.1.2.1;11.9.5.1.3.1.2.1 Variation 1: Reactions with Enols and Enolates;167
1.9.1.1.1.3.1.2.2;11.9.5.1.3.1.2.2 Variation 2: Reactions with Other Dipolarophiles;168
1.9.1.1.1.3.1.3;11.9.5.1.3.1.3 Method 3: Coupling of an Electron-Deficient Alkyne with a Nitroacetate;170
1.9.1.1.1.3.2;11.9.5.1.3.2 Fragments O--N--C--C and C;171
1.9.1.1.1.3.2.1;11.9.5.1.3.2.1 Method 1: From Dianions Derived from Oximes;171
1.9.1.1.1.3.2.1.1;11.9.5.1.3.2.1.1 Variation 1: Reactions of Oxime-Derived Dianions with Esters;171
1.9.1.1.1.4;11.9.5.1.4 By Formation of One Heteroatom--Heteroatom Bond;172
1.9.1.1.1.4.1;11.9.5.1.4.1 Fragment O--C--C--C--N;172
1.9.1.1.1.4.1.1;11.9.5.1.4.1.1 Method 1: Light-Induced Cycloaddition of 2-Cyanocycloalk-2-enones to Alkenes;172
1.9.1.1.1.5;11.9.5.1.5 By Formation of One Heteroatom--Carbon Bond;172
1.9.1.1.1.5.1;11.9.5.1.5.1 Fragment O--N--C--C--C;172
1.9.1.1.1.5.1.1;11.9.5.1.5.1.1 Method 1: Oxidative Cyclization of a,ß-Unsaturated Oximes;172
1.9.1.1.1.5.1.2;11.9.5.1.5.1.2 Method 2: Electrophilic Cyclization of Alkynyl O-Methyloximes;173
1.9.1.1.1.5.1.3;11.9.5.1.5.1.3 Method 3: Cyclization of 3-Oximinocarbonitriles;174
1.9.1.1.1.6;11.9.5.1.6 By Formation of One C--C Bond;175
1.9.1.1.1.6.1;11.9.5.1.6.1 Fragment C--O--N--C--C;175
1.9.1.1.1.6.1.1;11.9.5.1.6.1.1 Method 1: Cyclization of O-(ß-Oxoalkyl)-Substituted a-(Hydroxyimino)nitriles;175
1.9.1.1.2;11.9.5.2 Synthesis by Substituent Modification;176
1.9.1.1.2.1;11.9.5.2.1 Substitution of Existing Substituents;176
1.9.1.1.2.1.1;11.9.5.2.1.1 Of Halogens;176
1.9.1.1.2.1.1.1;11.9.5.2.1.1.1 By Carbofunctional Groups;176
1.9.1.1.2.1.1.1.1;11.9.5.2.1.1.1.1 Method 1: By Palladium-Catalyzed Cross Coupling;176
1.9.2;11.10 Product Class 10: 1,2-Benzisoxazoles and Related Compounds;180
1.9.2.1;11.10.5 1,2-Benzisoxazoles and Related Compounds;180
1.9.2.1.1;11.10.5.1 Synthesis by Ring-Closure Reactions;180
1.9.2.1.1.1;11.10.5.1.1 By Annulation to an Arene;180
1.9.2.1.1.1.1;11.10.5.1.1.1 By Formation of One O--C and One C--C Bond;180
1.9.2.1.1.1.1.1;11.10.5.1.1.1.1 Method 1: By 1,3-Dipolar Cycloaddition to Naphthoquinones;180
1.9.2.1.1.1.2;11.10.5.1.1.2 By Formation of One O--N Bond;181
1.9.2.1.1.1.2.1;11.10.5.1.1.2.1 Method 1: By Cyclization of 2-Hydroxyaryl Ketoximes and Aldoximes;181
1.9.2.1.1.1.2.2;11.10.5.1.1.2.2 Method 2: By Cyclization of N,2-Dihydroxybenzamides;182
1.9.2.1.1.1.3;11.10.5.1.1.3 By Formation of One O--C Bond;183
1.9.2.1.1.1.3.1;11.10.5.1.1.3.1 Method 1: By Cyclization of 2-Haloaryl Ketoximes;183
1.9.2.1.1.2;11.10.5.1.2 By Annulation to the Isoxazole Ring;184
1.9.2.1.1.2.1;11.10.5.1.2.1 Method 1: Cycloaddition to Isoxazoles;184
1.9.2.1.1.2.2;11.10.5.1.2.2 Method 2: Epoxide Ring Opening and Cyclization;185
1.9.2.1.1.2.3;11.10.5.1.2.3 Method 3: Annulation of a Hetarene;186
1.9.2.1.1.2.4;11.10.5.1.2.4 Method 4: Coupling of Diarylisoxazoles;188
1.9.2.1.2;11.10.5.2 Synthesis by Ring Transformation;189
1.9.2.1.2.1;11.10.5.2.1 Method 1: Rearrangement of Sultone Oximes;189
1.9.2.1.3;11.10.5.3 Aromatization;190
1.9.2.1.3.1;11.10.5.3.1 Method 1: Oxidative Aromatization of 4,5-Dihydro-1,2-benzisoxazoles;190
1.9.2.1.3.2;11.10.5.3.2 Method 2: Aromatization by Dehydrohalogenation;191
1.9.2.1.3.3;11.10.5.3.3 Method 3: Aromatization by Cleavage of N-Protected 2,3-Dihydro-1,2-benzisoxazoles;192
1.9.2.1.3.4;11.10.5.3.4 Method 4: Aromatization of Rings Fused to Isoxazoles;193
1.9.2.1.4;11.10.5.4 Synthesis by Substituent Modification;194
1.9.2.1.4.1;11.10.5.4.1 Substitution of Existing Substituents;195
1.9.2.1.4.1.1;11.10.5.4.1.1 Of Hydrogen;195
1.9.2.1.4.1.1.1;11.10.5.4.1.1.1 Method 1: Halogenation;195
1.9.2.1.4.1.2;11.10.5.4.1.2 Of Heteroatoms;196
1.9.2.1.4.1.2.1;11.10.5.4.1.2.1 Method 1: Substitution with Formation of a C--C Bond;196
1.9.3;11.13 Product Class 13: Benzoxazoles and Other Annulated Oxazoles;200
1.9.3.1;11.13.1 Synthesis by Ring-Closure Reactions;201
1.9.3.1.1;11.13.1.1 By Annulation to an Arene;201
1.9.3.1.1.1;11.13.1.1.1 By Formation of One O--C and One N--C Bond;201
1.9.3.1.1.1.1;11.13.1.1.1.1 Fragment O--C--C--C--N;201
1.9.3.1.1.1.1.1;11.13.1.1.1.1.1 Method 1: Synthesis from 2-Hydroxybenzoic Acids, Amides, or Azides;201
1.9.3.1.1.1.1.2;11.13.1.1.1.1.2 Method 2: Synthesis from 1-(2-Hydroxyphenyl)alkanone Oximes and Derivatives Thereof (Beckmann Rearrangement);202
1.9.3.1.1.1.2;11.13.1.1.1.2 Fragments O--C--C--N and C;204
1.9.3.1.1.1.2.1;11.13.1.1.1.2.1 Method 1: Synthesis from 2-Nitrophenols and Carbonic Acid Derivatives or Aldehydes;204
1.9.3.1.1.1.2.2;11.13.1.1.1.2.2 Method 2: Synthesis from 2-Aminophenols and Carbonic Acid Derivatives;206
1.9.3.1.1.1.2.2.1;11.13.1.1.1.2.2.1 Variation 1: Synthesis of 2-Alkoxybenzoxazoles or Benzoxazol-2(3H)-ones;206
1.9.3.1.1.1.2.2.2;11.13.1.1.1.2.2.2 Variation 2: Synthesis of Benzoxazole-2(3H)-thiones;209
1.9.3.1.1.1.2.2.3;11.13.1.1.1.2.2.3 Variation 3: Synthesis of Benzoxazol-2-amines;210
1.9.3.1.1.1.2.3;11.13.1.1.1.2.3 Method 3: Synthesis from 2-Aminophenols and Carboxylic Acid Derivatives;211
1.9.3.1.1.1.2.3.1;11.13.1.1.1.2.3.1 Variation 1: Using (Trihalomethyl)arenes or Carboxylic Acid Ortho Esters;211
1.9.3.1.1.1.2.3.2;11.13.1.1.1.2.3.2 Variation 2: Using Carboxylic Acids;212
1.9.3.1.1.1.2.3.3;11.13.1.1.1.2.3.3 Variation 3: Using Carboxylic Acid Chlorides;216
1.9.3.1.1.1.2.3.4;11.13.1.1.1.2.3.4 Variation 4: Using Carboxylic Acid Anhydrides or Imidates;217
1.9.3.1.1.1.2.3.5;11.13.1.1.1.2.3.5 Variation 5: Using Carboxamides;218
1.9.3.1.1.1.2.3.6;11.13.1.1.1.2.3.6 Variation 6: Using Nitriles;220
1.9.3.1.1.1.2.3.7;11.13.1.1.1.2.3.7 Variation 7: Using Carbon Monoxide and Aryl Halides;220
1.9.3.1.1.1.2.3.8;11.13.1.1.1.2.3.8 Variation 8: Using Isocyanides;221
1.9.3.1.1.1.2.4;11.13.1.1.1.2.4 Method 4: Synthesis from 2-Aminophenols and Aldehydes;222
1.9.3.1.1.1.2.5;11.13.1.1.1.2.5 Method 5: Synthesis from 2-Aminophenols and Alcohols;222
1.9.3.1.1.1.3;11.13.1.1.1.3 Fragments C--C and N--C--O;223
1.9.3.1.1.1.3.1;11.13.1.1.1.3.1 Method 1: Synthesis from 1,2-Dihaloarenes and Carboxamides;223
1.9.3.1.1.1.4;11.13.1.1.1.4 Fragments C--C--N and C--O;224
1.9.3.1.1.1.4.1;11.13.1.1.1.4.1 Method 1: Synthesis from 2-Bromoanilines and Carboxylic Acid Chlorides;224
1.9.3.1.1.2;11.13.1.1.2 By Formation of One C--O Bond;225
1.9.3.1.1.2.1;11.13.1.1.2.1 Fragment C--C--N--C--O;225
1.9.3.1.1.2.1.1;11.13.1.1.2.1.1 Method 1: Synthesis from N-(2-Haloaryl)carboxamides;225
1.9.3.1.1.2.1.2;11.13.1.1.2.1.2 Method 2: Synthesis from N-(3-Halophenyl)carboxamides;228
1.9.3.1.1.2.2;11.13.1.1.2.2 Fragment O--C--C--N--C;229
1.9.3.1.1.2.2.1;11.13.1.1.2.2.1 Method 1: Synthesis from N-(2-Hydroxyphenyl)thioureas;229
1.9.3.1.1.2.2.2;11.13.1.1.2.2.2 Method 2: Synthesis from N-(2-Hydroxyphenyl)ureas;230
1.9.3.1.1.2.2.3;11.13.1.1.2.2.3 Method 3: Synthesis from N-(2-Hydroxyphenyl)carboxamides;231
1.9.3.1.1.2.2.4;11.13.1.1.2.2.4 Method 4: Synthesis from 2-(Alkylidenamino)phenols;233
1.9.3.1.2;11.13.1.2 By Annulation to the Heterocyclic Ring;235
1.9.3.2;11.13.2 Synthesis by Ring Transformation;236
1.9.3.2.1;11.13.2.1 Method 1: Ring Contraction of 1,4-Benzoxazines;236
1.9.3.3;11.13.3 Synthesis by Substituent Modification;237
1.9.3.3.1;11.13.3.1 Substitution of Existing Substituents;237
1.9.3.3.1.1;11.13.3.1.1 Of Hydrogen;237
1.9.3.3.1.1.1;11.13.3.1.1.1 Method 1: Lithiation;237
1.9.3.3.1.1.2;11.13.3.1.1.2 Method 2: Arylation;238
1.9.3.3.1.1.3;11.13.3.1.1.3 Method 3: Halogenation;239
1.9.3.3.1.1.4;11.13.3.1.1.4 Method 4: Sulfanylation;240
1.9.3.3.1.1.5;11.13.3.1.1.5 Method 5: Nitration;241
1.9.3.3.1.1.6;11.13.3.1.1.6 Method 6: Amination;241
1.9.3.3.1.2;11.13.3.1.2 Of Metals;241
1.9.3.3.1.2.1;11.13.3.1.2.1 Method 1: Cross-Coupling Reactions;241
1.9.3.3.1.3;11.13.3.1.3 Of Halogen;242
1.9.3.3.1.3.1;11.13.3.1.3.1 Method 1: Cyanation of 2-Chlorobenzoxazoles;242
1.9.3.3.1.3.2;11.13.3.1.3.2 Method 2: Fluorination of 2-Chlorobenzoxazoles;243
1.9.3.3.1.3.3;11.13.3.1.3.3 Method 3: Alkoxy- or Aryloxylation of 2-Halobenzoxazoles;243
1.9.3.3.1.3.4;11.13.3.1.3.4 Method 4: Amination of 2-Chlorobenzoxazoles;243
1.9.3.3.1.4;11.13.3.1.4 Of Oxygen;244
1.9.3.3.1.4.1;11.13.3.1.4.1 Method 1: Thionation of Benzoxazol-2(3H)-ones;244
1.9.3.3.1.5;11.13.3.1.5 Of Sulfur;244
1.9.3.3.1.5.1;11.13.3.1.5.1 Method 1: Chlorination of Benzoxazole-2(3H)-thiones;244
1.9.3.3.1.5.2;11.13.3.1.5.2 Method 2: Alkoxylation of Benzoxazole-2(3H)-thiones;245
1.9.3.3.1.5.3;11.13.3.1.5.3 Method 3: Amination of Benzoxazole-2(3H)-thiones;246
1.9.3.3.2;11.13.3.2 Addition Reactions;246
1.9.3.3.2.1;11.13.3.2.1 Method 1: Synthesis of 3-Alkylbenzoxazolium Salts;246
1.9.3.3.3;11.13.3.3 Modification of Substituents;247
1.9.3.3.3.1;11.13.3.3.1 Method 1: S-Alkylation of Benzoxazole-2(3H)-thiones;247
1.9.3.3.3.2;11.13.3.3.2 Method 2: N-Alkylation of Benzoxazol-2-amines;248
1.9.4;11.15 Product Class 15: Isothiazoles;254
1.9.4.1;11.15.4 Isothiazoles;254
1.9.4.1.1;11.15.4.1 Synthesis by Ring-Closure Reactions;256
1.9.4.1.1.1;11.15.4.1.1 By Formation of One S--C and One N--C Bond;256
1.9.4.1.1.1.1;11.15.4.1.1.1 Method 1: By Cycloaddition of Thiazyl Chloride to a Furan or a Pyrrole;256
1.9.4.1.1.1.1.1;11.15.4.1.1.1.1 Variation 1: By Addition of Thiazyl Chloride to a Furan;256
1.9.4.1.1.1.2;11.15.4.1.1.2 Method 2: By 1,3-Dipolar Cycloaddition of Nitrile Sulfides to Alkynes and Alkenes;259
1.9.4.1.1.1.2.1;11.15.4.1.1.2.1 Variation 1: From 1,3,4-Oxathiazol-2-ones;259
1.9.4.1.1.1.2.2;11.15.4.1.1.2.2 Variation 2: From Difluoro(imino)-.4-sulfanes;260
1.9.4.1.1.2;11.15.4.1.2 By Formation of One S--N Bond;260
1.9.4.1.1.2.1;11.15.4.1.2.1 Method 1: By Oxidative Ring Closure of 3-Aminoprop-2-enyl Thiocarbonyl and Related Compounds;260
1.9.4.1.1.2.1.1;11.15.4.1.2.1.1 Variation 1: From 3-Aminoprop-2-enethioamides or 3-Aminoprop-2-enyl Thioketones;260
1.9.4.1.1.2.1.2;11.15.4.1.2.1.2 Variation 2: From (1E)-N-Hydroxy-3,3-bis(methylsulfanyl)prop-2-en-1-imines;267
1.9.4.1.1.2.1.3;11.15.4.1.2.1.3 Variation 3: From 2-[(Diphenyl-.4-sulfanylidene)amino]-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbothioamides;268
1.9.4.1.1.2.2;11.15.4.1.2.2 Method 2: From Bis(3-amino-3-oxopropyl) Disulfides;269
1.9.4.1.1.2.3;11.15.4.1.2.3 Method 3: From 3-Chloroprop-2-enals;269
1.9.4.1.1.2.4;11.15.4.1.2.4 Method 4: From 2-Sulfanylvinyl Ketones and O-Sulfonylhydroxylamines;270
1.9.4.1.1.2.5;11.15.4.1.2.5 Method 5: From tert-Butyl 2-Cyano-1,3,3,3-tetrafluoropropenyl Sulfide;271
1.9.4.1.1.3;11.15.4.1.3 By Formation of One C--C Bond;271
1.9.4.1.1.3.1;11.15.4.1.3.1 Method 1: By Base-Promoted Intramolecular Cyclization;271
1.9.4.1.1.3.1.1;11.15.4.1.3.1.1 Variation 1: Of Methyl [(Benzylsulfonyl)amino](oxo)acetate;272
1.9.4.1.2;11.15.4.2 Synthesis by Ring Transformation;272
1.9.4.1.2.1;11.15.4.2.1 Method 1: From 4,5-Dichloro-1,2,3-dithiazolium Chloride and Methyl 3-Aminocrotonate;272
1.9.4.1.3;11.15.4.3 Synthesis by Substituent Modification;273
1.9.4.1.3.1;11.15.4.3.1 Substitution of Existing Substituents;273
1.9.4.1.3.1.1;11.15.4.3.1.1 Of Heteroatoms;273
1.9.4.1.3.1.1.1;11.15.4.3.1.1.1 Method 1: Electrophilic Substitution;273
1.9.4.1.3.1.1.2;11.15.4.3.1.1.2 Method 2: Nucleophilic Substitution;275
1.9.4.1.3.1.1.2.1;11.15.4.3.1.1.2.1 Variation 1: Of Isothiazol-3-amine 1,1-Dioxides;275
1.9.4.1.3.1.1.2.2;11.15.4.3.1.1.2.2 Variation 2: Of Aryl 4,5-Dichloroisothiazol-3-yl Ketones and Related Compounds;277
1.9.4.1.3.1.1.3;11.15.4.3.1.1.3 Method 3: Isothiazole-5-carbaldehydes and 5-Alkylisothiazoles from Isothiazol-5-yllithiums;279
1.9.4.1.3.1.1.4;11.15.4.3.1.1.4 Method 4: Substitution of Halogens by Carbofunctional Groups;280
1.9.4.1.3.1.1.4.1;11.15.4.3.1.1.4.1 Variation 1: Castro-Stevens Coupling;280
1.9.4.1.3.1.1.4.2;11.15.4.3.1.1.4.2 Variation 2: Stille Coupling;280
1.9.4.1.3.1.1.4.3;11.15.4.3.1.1.4.3 Variation 3: Suzuki-and Negishi-like Couplings;281
1.9.4.1.3.1.1.4.4;11.15.4.3.1.1.4.4 Variation 4: Sonogashira and Ullmann Couplings;285
1.9.4.1.3.1.1.4.5;11.15.4.3.1.1.4.5 Variation 5: Heck Coupling;286
1.9.4.1.3.2;11.15.4.3.2 Addition Reactions;287
1.9.4.1.3.2.1;11.15.4.3.2.1 Addition of Organic Groups;287
1.9.4.1.3.2.1.1;11.15.4.3.2.1.1 Method 1: Annulation of a Heterocyclic Ring by 1,3-Dipolar Additions;287
1.9.4.1.3.2.1.2;11.15.4.3.2.1.2 Method 2: O-Alkylation of Isothiazol-3(2H)-ones;288
1.9.4.1.3.2.2;11.15.4.3.2.2 Addition of Heteroatoms;289
1.9.4.1.3.2.2.1;11.15.4.3.2.2.1 Method 1: Oxidation;289
1.9.4.1.3.2.2.2;11.15.4.3.2.2.2 Method 2: Amination;291
1.9.4.1.3.3;11.15.4.3.3 Modification of Substituents;292
1.9.4.1.3.3.1;11.15.4.3.3.1 Method 1: From Acylthiazoles;292
1.9.5;11.16 Product Class 16: Benzisothiazoles;296
1.9.5.1;11.16.3 Benzisothiazoles;296
1.9.5.1.1;11.16.3.1 1,2-Benzisothiazoles;296
1.9.5.1.1.1;11.16.3.1.1 Synthesis by Ring-Closure Reactions;297
1.9.5.1.1.1.1;11.16.3.1.1.1 By Formation of One S--C and One C--C Bond;297
1.9.5.1.1.1.2;11.16.3.1.1.2 By Formation of One S--N and/or One N--C Bond;298
1.9.5.1.1.1.2.1;11.16.3.1.1.2.1 Method 1: From Thiols, Disulfides, and Related Compounds;298
1.9.5.1.1.1.2.2;11.16.3.1.1.2.2 Method 2: From Oximes;299
1.9.5.1.1.1.2.3;11.16.3.1.1.2.3 Method 3: From (Aminosulfanyl)arenes;299
1.9.5.1.1.1.2.4;11.16.3.1.1.2.4 Method 4: From Disulfides;302
1.9.5.1.1.1.2.5;11.16.3.1.1.2.5 Method 5: From 2-Acylbenzenesulfonamides or 2-(Sulfinyl)benzamides;302
1.9.5.1.1.2;11.16.3.1.2 Synthesis by Substituent Modification;307
1.9.5.1.1.2.1;11.16.3.1.2.1 Substitution of Existing Substituents;307
1.9.5.1.1.2.1.1;11.16.3.1.2.1.1 Nucleophilic Substitution;307
1.9.5.1.1.2.2;11.16.3.1.2.2 Addition Reactions;307
1.9.5.1.1.2.2.1;11.16.3.1.2.2.1 Addition of Organic Groups;307
1.9.5.1.1.2.2.1.1;11.16.3.1.2.2.1.1 Method 1: Alkylation of Saccharins;307
1.9.5.1.1.2.2.1.2;11.16.3.1.2.2.1.2 Method 2: Alkylation of 4,6-Dinitro-1,2-benzisothiazole or 4,6-Dinitro-1,2-benzisothiazol-3(2H)-one;308
1.9.5.1.2;11.16.3.2 2,1-Benzisothiazoles;309
1.9.5.1.2.1;11.16.3.2.1 Synthesis by Ring Transformation;309
1.9.5.1.2.1.1;11.16.3.2.1.1 Method 1: From an Adduct of 3-Phenyl-2-thioxo-2,3-dihydrothieno[2,3-d]thiazol-6(5H)-one and N,N-Dimethyl-4-nitrosoaniline;309
1.9.5.1.2.2;11.16.3.2.2 Synthesis by Substituent Modification;310
1.9.5.1.2.2.1;11.16.3.2.2.1 Substitution of Existing Substituents;310
1.9.5.1.2.2.1.1;11.16.3.2.2.1.1 Of Hydrogen;310
1.9.6;11.17 Product Class 17: Thiazoles;314
1.9.6.1;11.17.6 Thiazoles;314
1.9.6.1.1;11.17.6.1 Synthesis by Ring-Closure Reactions;315
1.9.6.1.1.1;11.17.6.1.1 By Formation of Three Heteroatom--Carbon Bonds;315
1.9.6.1.1.1.1;11.17.6.1.1.1 By Formation of One S--C Bond and Two N--C Bonds;315
1.9.6.1.1.1.1.1;11.17.6.1.1.1.1 Fragments S--C, C--C, and N;315
1.9.6.1.1.1.1.1.1;11.17.6.1.1.1.1.1 Method 1: From a-Halo Ketones and Supported Reagents;315
1.9.6.1.1.2;11.17.6.1.2 By Formation of Two Heteroatom--Carbon Bonds and One C--C Bond;315
1.9.6.1.1.2.1;11.17.6.1.2.1 Fragments S--C, N--C, and C;315
1.9.6.1.1.2.1.1;11.17.6.1.2.1.1 Method 1: From Isothiocyanates, Cyanamide, and Acidic Methyl Halides;315
1.9.6.1.1.2.2;11.17.6.1.2.2 Fragments N--C--S, C, and C;316
1.9.6.1.1.2.2.1;11.17.6.1.2.2.1 Method 1: From Aldehydes, Haloforms, and Thiourea;316
1.9.6.1.1.2.2.2;11.17.6.1.2.2.2 Method 2: From Acid Chlorides, Ammonium Thiocyanate, Ethyl Bromopyruvate, and Tetramethylthiourea;317
1.9.6.1.1.2.3;11.17.6.1.2.3 Fragments C--N--C, C, and S;318
1.9.6.1.1.2.3.1;11.17.6.1.2.3.1 Method 1: From Dimethyl Cyanocarbonodithioimidoate, Activated Alkyl Halides, and a Sulfur Source;318
1.9.6.1.1.3;11.17.6.1.3 By Formation of Two Heteroatom--Carbon Bonds;319
1.9.6.1.1.3.1;11.17.6.1.3.1 Fragments C--C--N--C and S;319
1.9.6.1.1.3.1.1;11.17.6.1.3.1.1 Method 1: From N-Functionalized a-Aminonitriles;319
1.9.6.1.1.3.1.2;11.17.6.1.3.1.2 Method 2: From a-Acylamino Carbonyl Compounds;319
1.9.6.1.1.3.1.3;11.17.6.1.3.1.3 Method 3: From 2-Isocyanoacrylates;320
1.9.6.1.1.3.2;11.17.6.1.3.2 Fragments S--C--N and C--C;321
1.9.6.1.1.3.2.1;11.17.6.1.3.2.1 Method 1: From the Cyclocondensation of 1-Alkynyl(aryl)-.3-iodanes with Aminothiocarbonyl Compounds;321
1.9.6.1.1.3.2.2;11.17.6.1.3.2.2 Method 2: From a-Functionalized Carboxylic Acid Derivatives and Aminothiocarbonyl Compounds;323
1.9.6.1.1.3.2.2.1;11.17.6.1.3.2.2.1 Variation 1: From a-Functionalized Carboxyl Derivatives and Aminothiocarbonyl Compounds;323
1.9.6.1.1.3.2.2.2;11.17.6.1.3.2.2.2 Variation 2: From a-Functionalized Carbonitriles and Aminothiocarbonyl Compounds;324
1.9.6.1.1.3.2.3;11.17.6.1.3.2.3 Method 3: From a,ß-Unsaturated Carboxylic Acid Derivatives and Aminothiocarbonyl Compounds;325
1.9.6.1.1.3.2.4;11.17.6.1.3.2.4 Method 4: From a-Functionalized Ketones or Ketone Derivatives and Aminothiocarbonyl Compounds;326
1.9.6.1.1.3.2.4.1;11.17.6.1.3.2.4.1 Variation 1: From a-Diazo Ketones and Aminothiocarbonyl Compounds;326
1.9.6.1.1.3.2.4.2;11.17.6.1.3.2.4.2 Variation 2: From a-Halo and a,a-Dihalo Ketones and Aminothiocarbonyl Compounds;327
1.9.6.1.1.3.2.4.3;11.17.6.1.3.2.4.3 Variation 3: From a-Tosyloxy Ketones and Aminothiocarbonyl Compounds;329
1.9.6.1.1.3.2.4.4;11.17.6.1.3.2.4.4 Variation 4: From a-Dimethylsulfonio Ketones and Aminothiocarbonyl Compounds;331
1.9.6.1.1.3.2.4.5;11.17.6.1.3.2.4.5 Variation 5: From Ketones Halogenated In Situ and Aminothiocarbonyl Compounds;331
1.9.6.1.1.3.2.5;11.17.6.1.3.2.5 Method 5: From a,ß-Unsaturated Ketones and Aminothiocarbonyl Compounds;332
1.9.6.1.1.3.2.6;11.17.6.1.3.2.6 Method 6: From a-Halo Aldehydes, Acetals, or Enol Ethers and Aminothiocarbonyl Compounds;333
1.9.6.1.1.3.2.6.1;11.17.6.1.3.2.6.1 Variation 1: From a-Halo Aldehydes and Thioureas;333
1.9.6.1.1.3.2.6.2;11.17.6.1.3.2.6.2 Variation 2: From Ethyl 3-Ethoxyacrylate and Thioureas;334
1.9.6.1.1.3.2.6.3;11.17.6.1.3.2.6.3 Variation 3: From a-Halo Aldehydes and Thioamides;335
1.9.6.1.1.3.2.7;11.17.6.1.3.2.7 Method 7: From Enamines and Aminothiocarbonyl Compounds;336
1.9.6.1.1.3.2.8;11.17.6.1.3.2.8 Method 8: From 2,2,2-Trichloroethanols and Thioureas;337
1.9.6.1.1.3.2.9;11.17.6.1.3.2.9 Method 9: From 3-Haloalk-1-enes or 3-Haloalk-1-ynes and Aminothiocarbonyl Compounds;338
1.9.6.1.1.3.2.10;11.17.6.1.3.2.10 Method 10: From a-Halo Carbonyl Compounds and Thiocyanates;338
1.9.6.1.1.3.2.11;11.17.6.1.3.2.11 Method 11: From 1-Chloroalk-1-ynes and Aminothiocarbonyl Compounds;339
1.9.6.1.1.3.2.12;11.17.6.1.3.2.12 Method 12: From Allenes and Thioamides;340
1.9.6.1.1.3.3;11.17.6.1.3.3 Fragments C--C--S and C--N;340
1.9.6.1.1.3.3.1;11.17.6.1.3.3.1 Method 1: From 2-Sulfanylalkanoic Acids or Derivatives and Nitriles;340
1.9.6.1.1.3.4;11.17.6.1.3.4 Fragments C--C--N and C--S;342
1.9.6.1.1.3.4.1;11.17.6.1.3.4.1 Method 1: From a-Aminonitriles and Carbonyl Sulfide Sources;342
1.9.6.1.1.3.4.2;11.17.6.1.3.4.2 Method 2: From a-Amino Acids and Thiocarboxylic Acid Esters;343
1.9.6.1.1.3.4.3;11.17.6.1.3.4.3 Method 3: From Vinylamines and Chloroformylsulfenyl Chloride;343
1.9.6.1.1.3.4.4;11.17.6.1.3.4.4 Method 4: From Alk-2-ynylamines and Carbon Disulfide;344
1.9.6.1.1.3.5;11.17.6.1.3.5 Fragments C--C--S--C and N;345
1.9.6.1.1.3.5.1;11.17.6.1.3.5.1 Method 1: Cyclodehydration of S-(2-Oxoalkyl) Thioesters in the Presence of Ammonium Acetate;345
1.9.6.1.1.4;11.17.6.1.4 By Formation of One Heteroatom--Carbon and One C--C Bond;345
1.9.6.1.1.4.1;11.17.6.1.4.1 Fragments C--N--C--S and C;345
1.9.6.1.1.4.1.1;11.17.6.1.4.1.1 Method 1: From Resin-Bound N-Cyanocarbonimidodithioate and Functionalized Methyl Halides;345
1.9.6.1.1.4.1.2;11.17.6.1.4.1.2 Method 2: From N-Cyanocarbonimidodithioates and Acidic Methyl Halides;346
1.9.6.1.1.4.1.3;11.17.6.1.4.1.3 Method 3: From N-Cyanoimidothiocarbamates and Acidic Methyl Halides;346
1.9.6.1.1.4.1.4;11.17.6.1.4.1.4 Method 4: From N-(Diaminomethylene)- or N-[Amino(alkylsulfanyl)methylene]thioureas and a-Halo Ketones;347
1.9.6.1.1.4.1.5;11.17.6.1.4.1.5 Method 5: From N-(Aminomethylene)- or N-(Alkoxymethylene)thioureas and Acidic Methyl Halides;348
1.9.6.1.1.4.1.6;11.17.6.1.4.1.6 Method 6: From N-Acylthioureas and Acidic Methyl Halides;349
1.9.6.1.1.4.1.7;11.17.6.1.4.1.7 Method 7: From N-(Aminomethylene)- or N-(Hydroxymethylene)thioamides and Acidic Methyl Halides;350
1.9.6.1.1.4.2;11.17.6.1.4.2 Fragments C--N--C and S--C;351
1.9.6.1.1.4.2.1;11.17.6.1.4.2.1 Method 1: From N-Cyanoimidothioates and Sulfanylacetic Acid Derivatives;351
1.9.6.1.1.4.2.2;11.17.6.1.4.2.2 Method 2: From Alkyl Isocyanides and S--C Synthons;352
1.9.6.1.1.4.2.3;11.17.6.1.4.2.3 Method 3: From C-Aryl-N-methylglycines and S--C Synthons;352
1.9.6.1.1.5;11.17.6.1.5 By Formation of One Heteroatom--Carbon Bond;353
1.9.6.1.1.5.1;11.17.6.1.5.1 By Formation of One S--C Bond;353
1.9.6.1.1.5.1.1;11.17.6.1.5.1.1 Fragment C--C--N--C--S;353
1.9.6.1.1.5.1.1.1;11.17.6.1.5.1.1.1 Method 1: From N-Thiocarbonyl a-Amino Acids and Derivatives;353
1.9.6.1.1.5.1.1.2;11.17.6.1.5.1.1.2 Method 2: From a-(Thioacylamino)carbothioamides;354
1.9.6.1.1.5.1.1.3;11.17.6.1.5.1.1.3 Method 3: From a-Thioacylamino Acetals or a-(Thioacylamino)aldehydes;355
1.9.6.1.1.5.1.1.4;11.17.6.1.5.1.1.4 Method 4: From N-a-Haloacyl Isothiocyanates;356
1.9.6.1.1.5.1.1.5;11.17.6.1.5.1.1.5 Method 5: From Allenyl Isothiocyanates;357
1.9.6.1.1.5.1.1.6;11.17.6.1.5.1.1.6 Method 6: From N-[2,2-Dichloro-2-phenyl-1-(thioacetylamino)ethyl]benzenesulfonamide;358
1.9.6.1.1.5.1.1.7;11.17.6.1.5.1.1.7 Method 7: From ß-Hydroxy Thioamides;358
1.9.6.1.1.5.1.1.8;11.17.6.1.5.1.1.8 Method 8: From N-(2-Bromoalk-2-enyl)thioamides;359
1.9.6.1.1.5.1.1.9;11.17.6.1.5.1.1.9 Method 9: From 2,2-Dichloro-1-tosylvinyl Isothiocyanate and Various Nucleophiles;360
1.9.6.1.1.5.1.2;11.17.6.1.5.1.2 Fragment C--N--C--C--S;361
1.9.6.1.1.5.1.2.1;11.17.6.1.5.1.2.1 Method 1: From Di- and Tripeptides;361
1.9.6.1.1.5.1.2.2;11.17.6.1.5.1.2.2 Method 2: From Thiamine Disulfides;362
1.9.6.1.1.5.2;11.17.6.1.5.2 By Formation of One N--C Bond;364
1.9.6.1.1.5.2.1;11.17.6.1.5.2.1 Fragment C--C--S--C--N;364
1.9.6.1.1.5.2.1.1;11.17.6.1.5.2.1.1 Method 1: From a-Thiocyanato Carboxylic Acids and Derivatives;364
1.9.6.1.1.5.2.1.2;11.17.6.1.5.2.1.2 Method 2: From a-Imidoylsulfanyl Ketones;365
1.9.6.1.1.5.2.1.3;11.17.6.1.5.2.1.3 Method 3: From a-Thiocyanato Ketones;365
1.9.6.1.1.5.2.1.4;11.17.6.1.5.2.1.4 Method 4: From S-Alkynylisothiouronium or Thiobenzimidonium Salts and Base;366
1.9.6.1.1.5.2.1.5;11.17.6.1.5.2.1.5 Method 5: From 3-Aryl-2-thiocyanatopropanenitriles;367
1.9.6.1.1.5.2.1.6;11.17.6.1.5.2.1.6 Method 6: From 3-Thiocyanatoprop-1-ynes;368
1.9.6.1.1.5.2.2;11.17.6.1.5.2.2 Fragment C--S--C--C--N;368
1.9.6.1.1.5.2.2.1;11.17.6.1.5.2.2.1 Method 1: From 2-(Hydroxyimino)alkyl Dithiocarbonates;368
1.9.6.1.1.5.2.2.2;11.17.6.1.5.2.2.2 Method 2: From ß-Thiocyanatoenamines;369
1.9.6.1.1.6;11.17.6.1.6 By Formation of One C--C Bond;370
1.9.6.1.1.6.1;11.17.6.1.6.1 Fragment C--S--C--N--C;370
1.9.6.1.1.6.1.1;11.17.6.1.6.1.1 Method 1: From N-(1-Amino-2,2,2-trichloroethylidene)isothioureas;370
1.9.6.1.1.6.1.2;11.17.6.1.6.1.2 Method 2: From Alkyl N-Acylthioimidates;370
1.9.6.1.2;11.17.6.2 Synthesis by Ring Transformation;371
1.9.6.1.2.1;11.17.6.2.1 Method 1: By Ring Enlargement of Three-Membered Heterocycles;371
1.9.6.1.2.2;11.17.6.2.2 Method 2: By Formal Exchange of Ring Atoms with Retention of Ring Size;372
1.9.6.1.2.3;11.17.6.2.3 Method 3: By Ring Contraction of Heterocycles;373
1.9.6.1.3;11.17.6.3 Aromatization;374
1.9.6.1.3.1;11.17.6.3.1 Method 1: By Dehydration of Dihydrothiazoles;374
1.9.6.1.3.2;11.17.6.3.2 Method 2: Aromatization by Addition Reactions;375
1.9.6.1.3.2.1;11.17.6.3.2.1 Variation 1: Nucleophilic Additions to Exocyclic Double Bonds;375
1.9.6.1.3.2.2;11.17.6.3.2.2 Variation 2: S-Alkylation of Thiazole-2(3H)-thiones;376
1.9.6.1.3.2.3;11.17.6.3.2.3 Variation 3: S-Alkylation and N-Elimination of 3-Substituted Thiazole-2(3H)-thiones;377
1.9.6.1.3.2.4;11.17.6.3.2.4 Variation 4: N-Alkylation of 3-Substituted Thiazol-2(3H)-imines;377
1.9.6.1.3.3;11.17.6.3.3 Method 3: Elimination of Sulfur from Thiazole-2(3H)-thiones;378
1.9.6.1.3.4;11.17.6.3.4 Method 4: Base-Induced Conversion of 4,5-Dihydrothiazoles into Thiazoles;379
1.9.6.1.3.5;11.17.6.3.5 Method 5: Oxidation of 4,5-Dihydrothiazoles;380
1.9.6.1.3.6;11.17.6.3.6 Method 6: Oxidation of Thiazolidines;381
1.9.6.1.3.7;11.17.6.3.7 Method 7: Aromatization by Rearrangement (Isomerization);382
1.9.6.1.4;11.17.6.4 Synthesis from Other Thiazoles;383
1.9.6.1.4.1;11.17.6.4.1 Addition Reactions;383
1.9.6.1.4.1.1;11.17.6.4.1.1 Method 1: Quaternization;383
1.9.6.1.4.1.2;11.17.6.4.1.2 Method 2: Formation of Thiazole 3-Oxides;384
1.9.6.1.4.2;11.17.6.4.2 Synthesis by Substituent Modification;384
1.9.6.1.4.2.1;11.17.6.4.2.1 Method 1: Replacement of Hydrogen by Deuterium;384
1.9.6.1.4.2.2;11.17.6.4.2.2 Method 2: Replacement of Hydrogen by Metals;385
1.9.6.1.4.2.2.1;11.17.6.4.2.2.1 Variation 1: Replacement of Hydrogen by Magnesium or Zinc;385
1.9.6.1.4.2.2.2;11.17.6.4.2.2.2 Variation 2: Replacement of Hydrogen by Silicon or Tin;386
1.9.6.1.4.2.2.3;11.17.6.4.2.2.3 Variation 3: Replacement of Hydrogen by Boron;387
1.9.6.1.4.2.3;11.17.6.4.2.3 Method 3: Replacement of Hydrogen by Carbon Electrophiles;388
1.9.6.1.4.2.4;11.17.6.4.2.4 Method 4: Replacement of Hydrogen by Non-Carbon Electrophiles;392
1.9.6.1.4.2.4.1;11.17.6.4.2.4.1 Variation 1: Halogenation of Thiazoles;392
1.9.6.1.4.2.4.2;11.17.6.4.2.4.2 Variation 2: Introduction of Sulfo or Thiocyanato Groups;393
1.9.6.1.4.2.4.3;11.17.6.4.2.4.3 Variation 3: Introduction of Alkylsulfanyl or Arylsulfanyl Groups;394
1.9.6.1.4.2.4.4;11.17.6.4.2.4.4 Variation 4: Nitration of Thiazoles;395
1.9.6.1.4.2.4.5;11.17.6.4.2.4.5 Variation 5: Introduction of Arylazo Groups;396
1.9.6.1.4.2.4.6;11.17.6.4.2.4.6 Variation 6: Replacement of Hydrogen by Phosphorus;397
1.9.6.1.4.2.5;11.17.6.4.2.5 Method 5: Introduction of Amino Groups;397
1.9.6.1.4.3;11.17.6.4.3 Synthesis of Thiazoles from Metalated Thiazoles;399
1.9.6.1.4.3.1;11.17.6.4.3.1 Method 1: Replacement of Lithium, Magnesium, or Zinc by Carbon Electrophiles;399
1.9.6.1.4.3.2;11.17.6.4.3.2 Method 2: Replacement of Silyl Groups by Hydrogen;400
1.9.6.1.4.3.3;11.17.6.4.3.3 Method 3: Replacement of Silyl or Stannyl Groups by Carbon Electrophiles;401
1.9.6.1.4.3.4;11.17.6.4.3.4 Method 4: Replacement of Stannyl Groups by Halogens;404
1.9.6.1.4.3.5;11.17.6.4.3.5 Method 5: Replacement of Metals by Other Groups;405
1.9.6.1.4.3.5.1;11.17.6.4.3.5.1 Variation 1: Replacement of Lithium by Sulfur-Containing Reagents;405
1.9.6.1.4.3.6;11.17.6.4.3.6 Method 6: Modification of Other Substituents;406
1.9.6.1.4.3.6.1;11.17.6.4.3.6.1 Variation 1: Decarboxylation of Thiazolecarboxylic Acids and -carboxylates;406
1.9.6.1.4.3.6.2;11.17.6.4.3.6.2 Variation 2: Replacement of a Carbon Substituent by Nitrogen;407
1.9.6.1.4.3.6.3;11.17.6.4.3.6.3 Variation 3: Replacement of a Carbon Substituent by Halogen;407
1.9.6.1.4.3.6.4;11.17.6.4.3.6.4 Variation 4: Replacement of a Nitrogen Substituent by Hydrogen;408
1.9.6.1.4.3.6.5;11.17.6.4.3.6.5 Variation 5: Replacement of a Nitrogen Substituent by Carbon;408
1.9.6.1.4.3.6.6;11.17.6.4.3.6.6 Variation 6: Replacement of One Nitrogen Substituent by Another;409
1.9.6.1.4.3.6.7;11.17.6.4.3.6.7 Variation 7: Replacement of Nitrogen Substituents by Halogens;409
1.9.6.1.4.3.6.8;11.17.6.4.3.6.8 Variation 8: Replacement of Oxygen or Sulfur Groups by Hydrogen;410
1.9.6.1.4.3.6.9;11.17.6.4.3.6.9 Variation 9: Replacement of Oxygen or Sulfur Groups by Carbon-Containing Substituents;411
1.9.6.1.4.3.6.10;11.17.6.4.3.6.10 Variation 10: Replacement of Oxygen or Sulfur Substituents by Nitrogen;413
1.9.6.1.4.3.6.11;11.17.6.4.3.6.11 Variation 11: Replacement of Oxygen or Sulfur Substituents by Halogen;414
1.9.6.1.4.3.6.12;11.17.6.4.3.6.12 Variation 12: Replacement of Oxygen Substituents by Sulfur;415
1.9.6.1.4.3.6.13;11.17.6.4.3.6.13 Variation 13: Replacement of Sulfur Substituents by Oxygen;415
1.9.6.1.4.3.6.14;11.17.6.4.3.6.14 Variation 14: Replacement of One Sulfur Substituent by Another;416
1.9.6.1.4.3.6.15;11.17.6.4.3.6.15 Variation 15: Replacement of Halogen by Hydrogen;417
1.9.6.1.4.3.6.16;11.17.6.4.3.6.16 Variation 16: Replacement of Halogen by Carbon Nucleophiles;417
1.9.6.1.4.3.6.17;11.17.6.4.3.6.17 Variation 17: Replacement of Halogen by Nitrogen Substituents;418
1.9.6.1.4.3.6.18;11.17.6.4.3.6.18 Variation 18: Replacement of Halogen by Oxygen or Sulfur Substituents;419
1.9.6.1.4.3.6.19;11.17.6.4.3.6.19 Variation 19: Replacement of Halogen by Tin or Boron Substituents;419
1.9.6.1.5;11.17.6.5 Modification of Substituents;421
1.9.6.1.5.1;11.17.6.5.1 Modification of Carbofunctional Substituents;421
1.9.6.1.5.1.1;11.17.6.5.1.1 Method 1: Condensation at Alkyl Groups of Alkylthiazoles;421
1.9.6.1.5.1.2;11.17.6.5.1.2 Method 2: Other Transformations of Carbofunctional Substituents of Thiazoles;421
1.9.6.1.5.2;11.17.6.5.2 Modification of Heterofunctional Substituents;423
1.9.6.1.5.2.1;11.17.6.5.2.1 Method 1: Modification of O- and S-Substituents;423
1.9.6.1.5.3;11.17.6.5.3 Rearrangement of Substituents;424
1.9.7;11.18 Product Class 18: Benzothiazoles and Related Compounds;440
1.9.7.1;11.18.5 Benzothiazoles;440
1.9.7.1.1;11.18.5.1 Synthesis by Ring-Closure Reactions;441
1.9.7.1.1.1;11.18.5.1.1 By Annulation to an Arene or Hetarene Ring;441
1.9.7.1.1.1.1;11.18.5.1.1.1 By Formation of One S--C and One N--C Bond;441
1.9.7.1.1.1.1.1;11.18.5.1.1.1.1 Method 1: From 2-Amino(het)arenethiols;441
1.9.7.1.1.1.1.1.1;11.18.5.1.1.1.1.1 Variation 1: With Cyanamides;441
1.9.7.1.1.1.1.1.2;11.18.5.1.1.1.1.2 Variation 2: With Anhydrides;441
1.9.7.1.1.1.1.1.3;11.18.5.1.1.1.1.3 Variation 3: With Carboxylic Acids;441
1.9.7.1.1.1.1.1.4;11.18.5.1.1.1.1.4 Variation 4: With Aldehydes;442
1.9.7.1.1.1.2;11.18.5.1.1.2 By Formation of One S--C Bond;444
1.9.7.1.1.1.2.1;11.18.5.1.1.2.1 Method 1: From N-Arylthioureas;444
1.9.7.1.1.1.2.1.1;11.18.5.1.1.2.1.1 Variation 1: With a Leaving Group in the 2-Position;444
1.9.7.1.1.1.2.2;11.18.5.1.1.2.2 Method 2: From N-Arylthioamides;445
1.9.7.1.1.1.2.2.1;11.18.5.1.1.2.2.1 Variation 1: From 2-Unsubstituted N-Arylthioamides;445
1.9.7.1.1.1.2.2.2;11.18.5.1.1.2.2.2 Variation 2: From N-Arylthioamides with a Halogen or Hydroxy Leaving Group in the 2-Position;447
1.9.7.1.1.1.2.2.3;11.18.5.1.1.2.2.3 Variation 3: In Situ Formation from Amides;448
1.9.7.1.1.1.2.3;11.18.5.1.1.2.3 Method 3: From ortho-Nitrogen-Fuctionalized Aryl Disulfides;449
1.9.7.1.2;11.18.5.2 Synthesis by Substituent Modification;450
1.9.7.1.2.1;11.18.5.2.1 Substitution of Existing Substituents;450
1.9.7.1.2.1.1;11.18.5.2.1.1 Of Heteroatoms;450
1.9.7.1.2.1.1.1;11.18.5.2.1.1.1 Method 1: By Hetero Functions;450
1.9.8;11.20 Product Class 20: Isoselenazoles;452
1.9.8.1;11.20.3 Isoselenazoles;452
1.9.8.1.1;11.20.3.1 Synthesis by Ring-Closure Reactions;452
1.9.8.1.1.1;11.20.3.1.1 By Formation of One Se--N, One Se--C, and One N--C Bond;452
1.9.8.1.1.1.1;11.20.3.1.1.1 Fragments C--C--C, N, and Se;452
1.9.8.1.1.1.1.1;11.20.3.1.1.1.1 Method 1: Reaction of a,ß-Unsaturated ß-Chloroaldehydes with Potassium Selenocyanate and Ammonium Chloride;452
1.9.8.1.1.2;11.20.3.1.2 By Formation of One Se--N and One N--C Bond;454
1.9.8.1.1.2.1;11.20.3.1.2.1 Fragments Se-C--C--C and N;454
1.9.8.1.1.2.1.1;11.20.3.1.2.1.1 Method 1: Reaction of 4-(Methylselanyl)- or 4-(Phenylselanyl)-1,1,1-trihaloalk-3-en-2-ones with Bromine and Ammonia;454
1.9.8.1.1.2.1.2;11.20.3.1.2.1.2 Method 2: Reaction of ß-[(N,N-Dimethylcarbamoyl)selanyl]alkenyl Ketones and Hydroxylamine-O-sulfonic Acid;455
1.9.8.1.1.3;11.20.3.1.3 By Formation of One Se--N and One Se--C Bond;455
1.9.8.1.1.3.1;11.20.3.1.3.1 Fragments N--C--C--C and Se;455
1.9.8.1.1.3.1.1;11.20.3.1.3.1.1 Method 1: Reaction of Alkynone Oxime 4-Toluenesulfonates with Sodium Hydrogen Selenide or N,N-Dimethylselenocarbamate Ion;455
1.9.8.1.2;11.20.3.2 Synthesis by Substituent Modification;456
1.9.8.1.2.1;11.20.3.2.1 Modification of Substituents;456
1.9.8.1.2.1.1;11.20.3.2.1.1 Method 1: Reaction of 3-(Trichloromethyl)isoselenazoles with Sulfuric Acid;456
1.9.9;11.21 Product Class 21: Annulated Isoselenazole Compounds;460
1.9.9.1;11.21.5 Annulated Isoselenazole Compounds;460
1.9.9.1.1;11.21.5.1 Synthesis by Ring-Closure Reactions;460
1.9.9.1.1.1;11.21.5.1.1 By Formation of One Se--N and One N--C Bond;460
1.9.9.1.1.1.1;11.21.5.1.1.1 Fragments Se--Arene--C and N;460
1.9.9.1.1.1.1.1;11.21.5.1.1.1.1 Method 1: Reaction of 2-(Chloroselanyl)benzoyl Chloride with 4-Amino benzoic Acid;460
1.9.9.1.1.2;11.21.5.1.2 By Formation of One Se--N Bond;461
1.9.9.1.1.2.1;11.21.5.1.2.1 Fragment Se--Arene--C--N;461
1.9.9.1.1.2.1.1;11.21.5.1.2.1.1 Method 1: ortho-Metalation of Isophthalamides, Selenation, and Subsequent Oxidation;461
1.9.10;11.22 Product Class 22: Selenazoles;464
1.9.10.1;11.22.4 Selenazoles;464
1.9.10.1.1;11.22.4.1 Synthesis by Ring-Closure Reactions;464
1.9.10.1.1.1;11.22.4.1.1 By Formation of Two Se--C Bonds and One C--C Bond;464
1.9.10.1.1.1.1;11.22.4.1.1.1 Fragments C--N--C, Se, and C;464
1.9.10.1.1.1.1.1;11.22.4.1.1.1.1 Method 1: Reaction of Dithioimidocarbonates with Secondary Amines, Sodium Selenide, and Haloalkanes;464
1.9.10.1.1.2;11.22.4.1.2 By Formation of One Se--C and One N--C Bond;466
1.9.10.1.1.2.1;11.22.4.1.2.1 Fragments Se--C--N and C--C;466
1.9.10.1.1.2.1.1;11.22.4.1.2.1.1 Method 1: Reaction of Selenocarboxamides with a-Halocarbonyl Compounds;466
1.9.10.1.1.2.1.1.1;11.22.4.1.2.1.1.1 Variation 1: Reaction of Selenocarboxamides with a-Bromo Ketones;466
1.9.10.1.1.2.1.1.2;11.22.4.1.2.1.1.2 Variation 2: Reaction of Selenoformamide with a-Bromo Ketones;468
1.9.10.1.1.2.1.1.3;11.22.4.1.2.1.1.3 Variation 3: Reaction of Cyanoselenoamide or Bis(selenoamides) with a-Halocarbonyl Compounds;469
1.9.10.1.1.2.1.2;11.22.4.1.2.1.2 Method 2: Reaction of Selenocarboxamides with Acetylenic Compounds;470
1.9.10.1.1.2.1.3;11.22.4.1.2.1.3 Method 3: Cycloaddition of Selenocarboxamides with Selanyl Propadienyl Cations;471
1.9.10.1.1.2.1.4;11.22.4.1.2.1.4 Method 4: From Selenoureas and a-Halocarbonyl Compounds;472
1.9.10.1.1.2.1.4.1;11.22.4.1.2.1.4.1 Variation 1: Reaction of N-Phenylselenourea with 1,3-Dichloroacetone;472
1.9.10.1.1.2.1.4.2;11.22.4.1.2.1.4.2 Variation 2: Reaction of Selenourea or N-Benzoylselenourea with a-Halocarbonyl Compounds;475
1.9.10.1.1.2.1.4.3;11.22.4.1.2.1.4.3 Variation 3: Reaction of Selenourea with a-Bromo Ketones in the Presence of ß-Cyclodextrin;476
1.9.10.1.1.2.1.4.4;11.22.4.1.2.1.4.4 Variation 4: Reaction of Selenourea with a-Bromo-ß-oxo Esters in the Presence of ß-Cyclodextrin;477
1.9.10.1.1.2.1.4.5;11.22.4.1.2.1.4.5 Variation 5: Reaction of Selenourea with a-Bromo Ketones in the Presence of Copper(II) Chloride-Pyridine Complex;478
1.9.10.1.1.2.1.4.6;11.22.4.1.2.1.4.6 Variation 6: Reaction of Selenourea with 1-Aryl-2-bromoethanones in an Ionic Liquid/Water System;479
1.9.10.1.1.2.1.5;11.22.4.1.2.1.5 Method 5: From Selenoureas and a,ß-Unsaturated Carbonyl Compounds;481
1.9.10.1.1.2.1.5.1;11.22.4.1.2.1.5.1 Variation 1: Reaction of N,N-Dialkylselenoureas with a,ß-Unsaturated Ketones in the Presence of Iron(III) Chloride;481
1.9.10.1.1.2.1.5.2;11.22.4.1.2.1.5.2 Variation 2: Reaction of N,N-Dialkylselenoureas with a,ß-Unsaturated Aldehydes in the Presence of Iron(III) Chloride;482
1.9.10.1.1.2.1.5.3;11.22.4.1.2.1.5.3 Variation 3: Reaction of N,N-Dialkylselenoureas with 1,2-Dicarbonyl Compounds in the Presence of Iron(III) Chloride;482
1.9.10.1.1.2.1.6;11.22.4.1.2.1.6 Method 6: From Selenoureas and a-Haloacetonitriles;483
1.9.10.1.1.2.1.7;11.22.4.1.2.1.7 Method 7: From Selenoureas and Acetylenic Compounds;485
1.9.10.1.1.3;11.22.4.1.3 By Formation of One Se--C and One C--C Bond;485
1.9.10.1.1.3.1;11.22.4.1.3.1 Fragments Se--C--N--C and C;485
1.9.10.1.1.3.1.1;11.22.4.1.3.1.1 Method 1: From Selenazadienes and a-Halocarbonyl Compounds;485
1.9.10.1.1.3.1.1.1;11.22.4.1.3.1.1.1 Variation 1: Reaction of N,N-Dialkyl-N'-[(dimethylamino)methylene]selenoureas with Chloroacetyl Chloride;485
1.9.10.1.1.3.1.1.2;11.22.4.1.3.1.1.2 Variation 2: Reaction of N,N-Dialkyl-N'-[(dimethylamino)methylene]selenoureas and a-Halo Ketones;488
1.9.10.1.1.3.1.2;11.22.4.1.3.1.2 Method 2: From Selenazadienes and Chloroacetonitrile;489
1.9.10.1.1.3.2;11.22.4.1.3.2 Fragments C--N--C and Se--C;490
1.9.10.1.1.3.2.1;11.22.4.1.3.2.1 Method 1: From Dithioimidocarbonates and Ethaneselenothioates;490
1.9.10.1.1.4;11.22.4.1.4 By Formation of One C--C Bond;492
1.9.10.1.1.4.1;11.22.4.1.4.1 Fragment C--Se--C--N--C;492
1.9.10.1.1.4.1.1;11.22.4.1.4.1.1 Method 1: Cyclization of N-Acylcarbamimidoselenoates;492
1.9.10.1.2;11.22.4.2 Synthesis by Substituent Modification;493
1.9.10.1.2.1;11.22.4.2.1 By Halogenation and Alkylation of the Selenium Atom;493
1.9.10.1.2.1.1;11.22.4.2.1.1 Method 1: From Selenazoles to 1,1-Dihaloselenazoles and Se-Alkylselenazolium Ions;493
1.9.10.1.2.2;11.22.4.2.2 Synthesis by Modification of Substituents in the Side Chain;495
1.9.10.1.2.2.1;11.22.4.2.2.1 Method 1: Oxidation of 2-Benzylselenazoles and Subsequent Alkaline Hydrolysis;495
1.9.10.1.2.2.2;11.22.4.2.2.2 Method 2: Azo Coupling of Substituted Selenazol-2-amines;498
1.9.11;11.23 Product Class 23: Annulated Selenazole Compounds;502
1.9.11.1;11.23.3 Annulated Selenazole Compounds;502
1.9.11.1.1;11.23.3.1 Synthesis by Ring-Closure Reactions;502
1.9.11.1.1.1;11.23.3.1.1 By Annulation to an Arene;502
1.9.11.1.1.1.1;11.23.3.1.1.1 By Formation of Two Se--C Bonds;502
1.9.11.1.1.1.1.1;11.23.3.1.1.1.1 Fragments Arene--N--C and Se;502
1.9.11.1.1.1.1.1.1;11.23.3.1.1.1.1.1 Method 1: From 2-Halophenyl Isocyanides, Elemental Selenium, and Heteroatom Nucleophiles;502
1.9.11.1.1.2;11.23.3.1.2 By Annulation to a Selenazole;503
1.9.11.1.1.2.1;11.23.3.1.2.1 Method 1: Formation of 4-Chloro-1,2,3-triazines;503
1.9.11.1.2;11.23.3.2 Synthesis by Substituent Modification;504
1.9.11.1.2.1;11.23.3.2.1 Method 1: Modification of the Benzo Ring by Amination, Oxidation, and Substitution;504
1.9.11.1.2.2;11.23.3.2.2 Method 2: Modification of the Selenazole Ring by N-Alkylation and C--C Bond Formation on a Methyl Group at the C2 Position;505
1.9.11.1.2.2.1;11.23.3.2.2.1 Variation 1: Condensation with Ortho Esters or Imidamides;505
1.9.11.1.2.2.2;11.23.3.2.2.2 Variation 2: Condensation with Squaric Acid;508
1.9.11.1.2.2.3;11.23.3.2.2.3 Variation 3: Condensation with a Thiazole-5-carbaldehyde;510
1.9.12;11.25 Product Class 25: Isotellurazoles, and Annulated Isotellurazole and Tellurazole Compounds;514
1.9.12.1;11.25.4 Isotellurazoles, and Annulated Isotellurazole and Tellurazole Compounds;514
1.9.12.1.1;11.25.4.1 Isotellurazoles (1,2-Tellurazoles);514
1.9.12.1.1.1;11.25.4.1.1 Synthesis by Ring-Closure Reactions;514
1.9.12.1.1.1.1;11.25.4.1.1.1 By Formation of One Te--N and One N--C Bond;514
1.9.12.1.1.1.1.1;11.25.4.1.1.1.1 Fragments Te--C--C--C and N;514
1.9.12.1.1.1.1.1.1;11.25.4.1.1.1.1.1 Method 1: Reaction of ß-[(N,N-Dimethylcarbamoyl)tellanyl]alkenyl Ketones with Hydroxylamine-O-sulfonic Acid;514
1.9.12.1.1.1.2;11.25.4.1.1.2 By Formation of One Te--N and One Te--C Bond;516
1.9.12.1.1.1.2.1;11.25.4.1.1.2.1 Fragments N--C--C--C and Te;516
1.9.12.1.1.1.2.1.1;11.25.4.1.1.2.1.1 Method 1: Reaction of Alkynone Oxime 4-Toluenesulfonates with N,N-Dimethyltellurocarbamate Ion;516
1.9.12.1.2;11.25.4.2 1,2-Benzisotellurazoles;517
1.9.12.1.2.1;11.25.4.2.1 Synthesis by Ring-Closure Reactions;517
1.9.12.1.2.1.1;11.25.4.2.1.1 By Formation of One N--Te Bond;517
1.9.12.1.2.1.1.1;11.25.4.2.1.1.1 Fragment Te--Arene--C--N;517
1.9.12.1.2.1.1.1.1;11.25.4.2.1.1.1.1 Method 1: ortho-Metalation of Isophthalamides, Telluration, and Subsequent Oxidation;517
1.9.12.1.3;11.25.4.3 Benzotellurazoles;518
1.9.12.1.3.1;11.25.4.3.1 Synthesis by Ring-Closure Reactions;518
1.9.12.1.3.1.1;11.25.4.3.1.1 By Formation of Two Te--C Bonds;518
1.9.12.1.3.1.1.1;11.25.4.3.1.1.1 Fragments Arene--N--C and Te;518
1.9.12.1.3.1.1.1.1;11.25.4.3.1.1.1.1 Method 1: Copper(I)-Cataly zed Reaction of 2-Iodophenyl Isocyanide with Tellurium and an Amine Nucleophile;518
1.10;Volume 16: Six-Membered Hetarenes with Two Identical Heteroatoms;520
1.10.1;16.20 Product Class 20: Pyridopyrazines;520
1.10.1.1;16.20.3 Pyridopyrazines;520
1.10.1.1.1;16.20.3.1 Pyrido[2,3-b]pyrazines;522
1.10.1.1.1.1;16.20.3.1.1 Synthesis by Ring-Closure Reactions;522
1.10.1.1.1.1.1;16.20.3.1.1.1 By Formation of Two N--C Bonds;522
1.10.1.1.1.1.1.1;16.20.3.1.1.1.1 Method 1: Condensation of Pyridine-2,3-diamines with Dicarbonyl Compounds;522
1.10.1.1.1.1.1.2;16.20.3.1.1.1.2 Method 2: Reaction of Pyridine-2,3-diamine with Alloxane or Epoxides;525
1.10.1.1.1.1.1.3;16.20.3.1.1.1.3 Method 3: Reaction of Pyridine-2,3-diamine with Ethoxy(imino)acetates;526
1.10.1.1.1.1.2;16.20.3.1.1.2 By Formation of One N--C Bond;526
1.10.1.1.1.1.2.1;16.20.3.1.1.2.1 Method 1: Phosphoryl Chloride Mediated Heteroannulation of N,S-Acetals;526
1.10.1.1.1.2;16.20.3.1.2 Synthesis by Substituent Modification;527
1.10.1.1.2;16.20.3.2 Pyrido[3,4-b]pyrazines;529
1.10.1.1.2.1;16.20.3.2.1 Synthesis by Ring-Closure Reactions;529
1.10.1.1.2.1.1;16.20.3.2.1.1 By Formation of Two N--C Bonds;529
1.10.1.1.2.1.1.1;16.20.3.2.1.1.1 Method 1: Condensation of Pyridine-3,4-diamines with Dicarbonyl Compounds;529
1.10.1.1.2.2;16.20.3.2.2 Synthesis by Substituent Modification;530
1.11;Volume 31: Arene-X (X = Hal, O, S, Se, Te, N, P);534
1.11.1;31.4 Product Class 4: Aryl Iodine Compounds;534
1.11.1.1;31.4.2.2 Iodoarenes;534
1.11.1.1.1;31.4.2.2.1 Synthesis of Iodoarenes;534
1.11.1.1.1.1;31.4.2.2.1.1 Method 1: Electrophilic Iodination;534
1.11.1.1.1.1.1;31.4.2.2.1.1.1 Variation 1: Of Fluorophenols;534
1.11.1.1.1.2;31.4.2.2.1.2 Method 2: Iodination by Hunsdiecker-Type Decarboxylation;537
1.11.1.1.1.2.1;31.4.2.2.1.2.1 Variation 1: Using Classical Reagents (Silver, Mercury, or Thallium Salts);537
1.11.1.1.1.2.2;31.4.2.2.1.2.2 Variation 2: Using the Barton Modification;538
1.11.1.1.1.3;31.4.2.2.1.3 Method 3: Iodination of Quinones;539
1.11.1.1.1.3.1;31.4.2.2.1.3.1 Variation 1: Using an Iodine Addition-Elimination Sequence;539
1.11.1.1.1.3.2;31.4.2.2.1.3.2 Variation 2: Using an Addition-Oxidation Sequence;542
1.11.1.1.1.3.3;31.4.2.2.1.3.3 Variation 3: Using Hypervalent Iodine Compounds;543
1.12;Author Index;546
1.13;Abbreviations;576
1.14;List of All Volumes;582mehr
Leseprobe
Abstracts
5.1.1.8 Germanium Hydrides

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of germanium hydrides, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · hydrides · germyl hydride · germanium hydride · radical reduction · hydrogermylation · germylation · tris(2-furyl)germane · cross coupling · germyl cation
5.1.15.2 Germanium Cyanides

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of germanium cyanides, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · cyanides · cyanation · halides · silver · germole
5.1.16.6 Acylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of acylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · enol ethers · [2+2] cycloaddition · azetidines · BINAP · alkynes · carbonylation · furans · radicals · polymerization · amides
5.1.18.4 -Halo- and -Alkoxyvinylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of -halo- and -alkoxyvinylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · substitution · hydrometalation · carbometalation · halogenation · alkynes · germatranes · desulfonylation · cross coupling · palladium(0) · styrenes
5.1.19.7 -Halo-, -Hydroxy,- -Alkoxy-, and -Aminoalkylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of -halo-, -hydroxy-, -alkoxy-, and -aminoalkylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · [1,2] rearrangements · oxo-carbenium · oxonium · substitution · hydroboration · boronic ester · [3+2] cycloaddition · germenes · silylation · borylation
5.1.20.4 Alkynylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of alkynylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · alkynes · [3+2] cycloadditions · hydrostannylation · hydroboration · cross coupling · palladium(0) · substitution · cross metathesis · elimination · PausonKhand reaction · cyclopentenones
5.1.22.6 Aryl- and Heteroarylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of aryl- and heteroarylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · cross coupling · Stille reaction · HiyamaDenmark reaction · substitution · Barbier conditions · transmetalation · cycloaddition · solid-phase synthesis · traceless linkers
5.1.23.6 Vinylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of vinylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · vinylgermanes · alkenylgermanes · -effect · hyperconjugation · hydrogermylation · heterogermylation · metallogermylation · cross coupling · germatranes
5.1.24.4 Propargyl- and Allenylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of propargyl- and allenylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · propargylgermanes · allenylgermanes · transmetalation · Grignard reagents · [2+2] cycloaddition
5.1.25.3 Benzylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of benzylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · benzylgermanes · cross coupling · boscalid
5.1.26.6 Allylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of allylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · alkenylgermanes · allylation · germylene · -allylpalladium(0) · metallogermanes · BaylisHillman · germyl radicals
5.1.27.4 Alkylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of alkylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 20012009.

Keywords: germanes · germanium compounds · alkenylgermanes · ADMET · germylene · hydrogermylation
9.11.4 Selenophenes

J. Schatz and M. Seßler

This manuscript is intended to update the first report on the synthesis of selenophenes in Science of Synthesis and will briefly summarize essential, more recent findings concerning this heterocyclic system in the first decade of the new millennium. During this time, applications of selenophene-based materials in organic electronics and photonics received considerable interest, and selenophene-containing -conjugated compounds have been proposed as organic magnetic materials.

Keywords: selenophenes · active methylene compounds · selanylenynes · cyclization · aromatization · metalhalogen exchange
9.12.3 Tellurophenes

J. Schatz and M. Seßler

This manuscript is intended to update the earlier report on the synthesis of tellurophenes in Science of Synthesis, and summarizes essential, more recent findings concerning this heterocyclic system in the first decade of the new millennium. The decade 20002010 saw an increasing interest in organic molecules as functional materials, shifting the focus away from biological or pharmaceutical application. This trend could especially be observed for thiophenes, leading, not surprisingly, also to an increasing pursuit of potential applications of tellurophenes.

Keywords: tellurophenes · tellanylenynes · cyclization · aryl cross coupling
11.9.5 Isoxazoles

P. Margaretha

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of isoxazoles (1,2-oxazoles). It focuses on the literature published in the period 20012009.

Keywords: isoxazoles · isoxazol-5-ones · dipolar cycloadditions · oximes · nitrile oxides · cyclization · multicomponent coupling · regioselectivity
11.10.5 1,2-Benzisoxazoles and Related Compounds

S. Härtinger

This update deals with...
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