E-Book, Englisch, 572 Seiten, PDF, Format (B × H): 170 mm x 240 mm
Reihe: Science of Synthesis
E-Book, Englisch, 572 Seiten, PDF, Format (B × H): 170 mm x 240 mm
Reihe: Science of Synthesis
ISBN: 978-3-13-178711-8
Verlag: Thieme
Format: PDF
Kopierschutz: Adobe DRM (»Systemvoraussetzungen)
Content of this volume: Dialkyl- and Diarylmagnesiums, 1H- and 2H-Indazoles, Quinolizinium Salts and Benzo Analogues, 1,2-Diselenins, 1,4-Diselenins, Pyrimidines, Acyclic Dialkyl Selenoxides and Derivatives.
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Weitere Infos & Material
1;Science of Synthesis: Knowledge Updates 2011/1;1
1.1;Title page;5
1.2;Imprint;7
1.3;Preface;8
1.4;Abstracts;10
1.5;Overview;14
1.6;Table of Contents;16
1.7;Volume 7: Compounds of Groups 13 and 2 (Al, Ga, In, Tl, Be ··· Ba);34
1.7.1;7.6 Product Class 6: Magnesium Compounds;34
1.7.1.1;7.6.15 Product Subclass 15: Dialkyl- and Diarylmagnesiums;34
1.7.1.1.1;Synthesis of Product Subclass 15;34
1.7.1.1.1.1;7.6.15.1 Method 1: Disproportion of Grignard Reagents;34
1.7.1.1.1.1.1;7.6.15.1.1 Variation 1: Reaction of Magnesium Metal with 2-Chlorobutane;35
1.7.1.1.1.2;7.6.15.2 Method 2: Reaction of Grignard Reagents with Organolithium Reagents;35
1.7.1.1.1.2.1;7.6.15.2.1 Variation 1: Reaction of Activated Magnesium Halides with Organolithium Reagents;36
1.7.1.1.1.3;7.6.15.3 Method 3: Reaction of Diorganomercury(II) Compounds with Magnesium Metal;37
1.7.1.1.1.4;7.6.15.4 Method 4: Reaction of Alkenes and Activated Magnesium Hydride;37
1.7.1.1.1.5;7.6.15.5 Method 5: Reaction of 1,3-Dienes with Activated Magnesium Metal;38
1.7.1.1.2;Applications of Product Subclass 15 in Organic Synthesis;39
1.7.1.1.2.1;7.6.15.6 Method 6: Reactions of Organomagnesium Compounds;39
1.7.1.1.2.2;7.6.15.7 Method 7: Reactions Involving Diorganomagnesium Compounds Obtained from 1,3-Dienes;42
1.7.1.1.2.3;7.6.15.8 Method 8: Catalysts Derived from Diorganomagnesium Compounds;43
1.7.1.1.2.4;7.6.15.9 Method 9: Miscellaneous Reactions of Diorganomagnesium Compounds;44
1.8;Volume 12: Five-Membered Hetarenes with Two Nitrogen or Phosphorus Atoms;48
1.8.1;12.2 Product Class 2: 1H- and 2H-Indazoles;48
1.8.1.1;12.2.5 1H- and 2H-Indazoles;48
1.8.1.1.1;12.2.5.1 Synthesis by Ring-Closure Reactions;49
1.8.1.1.1.1;12.2.5.1.1 By Annulation to an Arene;49
1.8.1.1.1.1.1;12.2.5.1.1.1 By Formation of One N--N and One N--C Bond;49
1.8.1.1.1.1.1.1;12.2.5.1.1.1.1 Fragments N--Arene--C and N;49
1.8.1.1.1.1.1.1.1;12.2.5.1.1.1.1.1 Method 1: From 2-Alkylanilines by Diazotization or Nitrosation;49
1.8.1.1.1.1.1.1.2;12.2.5.1.1.1.1.2 Method 2: From 2-Acylnitroarenes;50
1.8.1.1.1.1.2;12.2.5.1.1.2 By Formation of Two N--C Bonds;51
1.8.1.1.1.1.2.1;12.2.5.1.1.2.1 Fragment Arene--C and N--N;51
1.8.1.1.1.1.2.1.1;12.2.5.1.1.2.1.1 Method 1: From 1-Acyl-2-haloarenes and Hydrazine;51
1.8.1.1.1.1.2.1.2;12.2.5.1.1.2.1.2 Method 2: From 1-Alkyl-2-haloarenes and Hydrazines;53
1.8.1.1.1.1.2.1.3;12.2.5.1.1.2.1.3 Method 3: From 2-Arylidenecyclohexanones and Hydrazines;54
1.8.1.1.1.1.2.1.4;12.2.5.1.1.2.1.4 Method 4: From 2-Acylcyclohexanones and Hydrazine;55
1.8.1.1.1.1.2.1.5;12.2.5.1.1.2.1.5 Method 5: From 2-Acylhydroxyarenes and Hydrazine;56
1.8.1.1.1.1.2.1.6;12.2.5.1.1.2.1.6 Method 6: From [2-(Halomethyl)aryl]zincs and Arenediazonium Salts;56
1.8.1.1.1.1.2.2;12.2.5.1.1.2.2 Fragments Arene and N--N--C;57
1.8.1.1.1.1.2.2.1;12.2.5.1.1.2.2.1 Method 1: From Benzyne and Diazo Compounds;57
1.8.1.1.1.1.2.2.1.1;12.2.5.1.1.2.2.1.1 Variation 1: Using Acyl Diazomethanes;58
1.8.1.1.1.1.2.2.1.2;12.2.5.1.1.2.2.1.2 Variation 2: Using (Trimethylsilyl)diazomethane;59
1.8.1.1.1.1.2.2.1.3;12.2.5.1.1.2.2.1.3 Variation 3: Using Sydnones;61
1.8.1.1.1.1.2.2.1.4;12.2.5.1.1.2.2.1.4 Variation 4: Using Azomethine Imides;61
1.8.1.1.1.1.2.2.2;12.2.5.1.1.2.2.2 Method 2: From Quinones and Arylhydrazones;62
1.8.1.1.1.1.2.2.3;12.2.5.1.1.2.2.3 Method 3: From Nitroarenes or Nitroalkenes and Hydrazones;63
1.8.1.1.1.1.3;12.2.5.1.1.3 By Formation of One N--C and One C--C Bond;63
1.8.1.1.1.1.3.1;12.2.5.1.1.3.1 Fragments N--N--Arene and C;63
1.8.1.1.1.1.3.1.1;12.2.5.1.1.3.1.1 Method 1: From Arylhydrazines and Acyl Derivatives;63
1.8.1.1.1.1.3.1.2;12.2.5.1.1.3.1.2 Method 2: From Arylhydrazones;65
1.8.1.1.1.1.3.1.3;12.2.5.1.1.3.1.3 Method 3: By Carbonylation;65
1.8.1.1.1.1.4;12.2.5.1.1.4 By Formation of One N--N Bond;65
1.8.1.1.1.1.4.1;12.2.5.1.1.4.1 Fragment N–Arene–C--N;65
1.8.1.1.1.1.4.1.1;12.2.5.1.1.4.1.1 Method 1: From 2-Acylamino- or 2-Acylazidoarenes;65
1.8.1.1.1.1.4.1.1.1;12.2.5.1.1.4.1.1.1 Variation 1: Using Oximes;65
1.8.1.1.1.1.4.1.1.2;12.2.5.1.1.4.1.1.2 Variation 2: From 2-Amino- and 2-Azidobenzamides;66
1.8.1.1.1.1.4.1.2;12.2.5.1.1.4.1.2 Method 2: From 1-Acyl-2-nitroarenes;67
1.8.1.1.1.1.4.1.2.1;12.2.5.1.1.4.1.2.1 Variation 1: From 2-Nitroiminoarenes;67
1.8.1.1.1.1.4.1.2.2;12.2.5.1.1.4.1.2.2 Variation 2: From 2-Nitrobenzamides;68
1.8.1.1.1.1.4.1.3;12.2.5.1.1.4.1.3 Method 3: From 1-(Aminomethyl)-2-nitroarenes;68
1.8.1.1.1.1.5;12.2.5.1.1.5 By Formation of One N--C Bond;70
1.8.1.1.1.1.5.1;12.2.5.1.1.5.1 Fragment N--N--Arene--C;70
1.8.1.1.1.1.5.1.1;12.2.5.1.1.5.1.1 Method 1: From (2-Alkynylphenyl)triazenes;70
1.8.1.1.1.1.5.1.2;12.2.5.1.1.5.1.2 Method 2: From Azoarenes;71
1.8.1.1.1.1.5.1.2.1;12.2.5.1.1.5.1.2.1 Variation 1: From 2-Diazenylbenzonitriles or (2-Ethynylphenyl)diazenes;71
1.8.1.1.1.1.5.1.2.2;12.2.5.1.1.5.1.2.2 Variation 2: From 2-Acyl-1-diazenylarenes or 2-(Phenyldiazenyl)benzhydrols;71
1.8.1.1.1.1.5.1.3;12.2.5.1.1.5.1.3 Method 3: From 2-Hydrazinobenzonitriles;72
1.8.1.1.1.1.5.2;12.2.5.1.1.5.2 Fragment N--N--C--Arene;72
1.8.1.1.1.1.5.2.1;12.2.5.1.1.5.2.1 Method 1: From (2-Halobenzyl)hydrazines and 2-Halobenzohydrazides;72
1.8.1.1.1.1.5.2.2;12.2.5.1.1.5.2.2 Method 2: From (2-Halobenzylidene)hydrazines;73
1.8.1.1.1.1.5.2.3;12.2.5.1.1.5.2.3 Method 3: From (2-Nitrobenzylidene)hydrazines;74
1.8.1.1.1.1.5.2.4;12.2.5.1.1.5.2.4 Method 4: From Benzophenone Hydrazones;75
1.8.1.1.1.1.6;12.2.5.1.1.6 By Formation of One C--C Bond;75
1.8.1.1.1.1.6.1;12.2.5.1.1.6.1 Fragment Arene--N--N--C;75
1.8.1.1.1.1.6.1.1;12.2.5.1.1.6.1.1 Method 1: From 2-Alkylidenehydrazinoarenes;75
1.8.1.1.1.2;12.2.5.1.2 By Annulation to the Heterocyclic Ring;76
1.8.1.1.1.2.1;12.2.5.1.2.1 By Formation of Two C--C Bonds;76
1.8.1.1.1.2.1.1;12.2.5.1.2.1.1 Fragments Pyrazole--C--C and C--C;76
1.8.1.1.1.2.1.1.1;12.2.5.1.2.1.1.1 Method 1: From 4-Styrylpyrazoles and Dienophiles;76
1.8.1.1.1.2.1.2;12.2.5.1.2.1.2 Fragments C--Pyrazole--C and C--C;76
1.8.1.1.1.2.1.2.1;12.2.5.1.2.1.2.1 Method 1: From Dihydropyrazol-3-ones and Dienophiles;76
1.8.1.1.1.2.1.2.2;12.2.5.1.2.1.2.2 Method 2: From Pyrazole-4,5-quinodimethane and Dienophiles;77
1.8.1.1.1.2.1.3;12.2.5.1.2.1.3 Fragments C--Pyrazole and C--C--C;78
1.8.1.1.1.2.1.3.1;12.2.5.1.2.1.3.1 Method 1: From 5-(Cyanomethyl)pyrazoles and a-Oxoketene Dithioacetals;78
1.8.1.1.1.2.2;12.2.5.1.2.2 By Formation of One C--C Bond;78
1.8.1.1.1.2.2.1;12.2.5.1.2.2.1 Fragment C--C--Pyrazole--C--C;78
1.8.1.1.1.2.2.1.1;12.2.5.1.2.2.1.1 Method 1: From 5-Phenyl-4-styryl-1H-pyrazoles or 1-(5-Phenyl-1H-pyrazol-4-yl)-2-phenylethanol;78
1.8.1.1.1.2.2.1.2;12.2.5.1.2.2.1.2 Method 2: From 3,4-Diethynyl-1H-pyrazoles;79
1.8.1.1.1.3;12.2.5.1.3 From Acyclic Reactants;79
1.8.1.1.1.3.1;12.2.5.1.3.1 Method 1: From Alkenylethynyl Carbenes;79
1.8.1.1.2;12.2.5.2 Synthesis By Ring Transformation;80
1.8.1.1.2.1;12.2.5.2.1 Formal Exchange of Ring Members with Retention of Ring Size;80
1.8.1.1.2.1.1;12.2.5.2.1.1 Method 1: Of a Five-Membered Heterocycle;80
1.8.1.1.2.2;12.2.5.2.2 Ring Contraction;82
1.8.1.1.2.2.1;12.2.5.2.2.1 Method 1: Of a Six-Membered Heterocycle;82
1.8.1.1.2.2.2;12.2.5.2.2.2 Method 2: Of a Seven-Membered Heterocycle;83
1.8.1.1.2.2.3;12.2.5.2.2.3 Method 3: Of a Seven-Membered Carbocycle;83
1.8.1.1.3;12.2.5.3 Aromatization;84
1.8.1.1.3.1;12.2.5.3.1 Method 1: Of a Six-Membered Carbocycle;84
1.8.1.1.4;12.2.5.4 Synthesis By Substituent Modification;85
1.8.1.1.4.1;12.2.5.4.1 Addition Reactions;85
1.8.1.1.4.1.1;12.2.5.4.1.1 Addition of Organic Groups;85
1.8.1.1.4.1.1.1;12.2.5.4.1.1.1 Method 1: Addition of Alkyl Groups;85
1.8.1.1.4.1.1.2;12.2.5.4.1.1.2 Method 2: Addition of a Ring System to the Heterocyclic Ring;85
1.8.1.1.4.1.2;12.2.5.4.1.2 Addition of Heteroatoms;86
1.8.1.1.4.1.2.1;12.2.5.4.1.2.1 Method 1: By Oxidation;86
1.8.1.1.4.1.2.2;12.2.5.4.1.2.2 Method 2: Reduction of the Heterocyclic Ring;87
1.8.1.1.4.2;12.2.5.4.2 Substitution of Existing Substituents;87
1.8.1.1.4.2.1;12.2.5.4.2.1 Of Hydrogen;87
1.8.1.1.4.2.1.1;12.2.5.4.2.1.1 Method 1: Metalation;87
1.8.1.1.4.2.1.1.1;12.2.5.4.2.1.1.1 Variation 1: Lithiation;87
1.8.1.1.4.2.1.1.2;12.2.5.4.2.1.1.2 Variation 2: Metalation by Transition Metals;88
1.8.1.1.4.2.1.2;12.2.5.4.2.1.2 Method 2: Halogenation;89
1.8.1.1.4.2.1.3;12.2.5.4.2.1.3 Method 3: Alkoxylation;90
1.8.1.1.4.2.1.4;12.2.5.4.2.1.4 Method 4: Alkylation;90
1.8.1.1.4.2.1.5;12.2.5.4.2.1.5 Method 5: Arylation;93
1.8.1.1.4.2.1.6;12.2.5.4.2.1.6 Method 6: Acylation;94
1.8.1.1.4.2.2;12.2.5.4.2.2 Of Heteroatoms;95
1.8.1.1.4.2.2.1;12.2.5.4.2.2.1 Method 1: Halogen–Metal Exchange;95
1.8.1.1.4.2.2.2;12.2.5.4.2.2.2 Method 2: Cross-Coupling Reactions of Haloindazoles;96
1.8.1.1.4.2.2.3;12.2.5.4.2.2.3 Method 3: Removal or Exchange of Silyl Groups;97
1.8.1.1.4.2.2.4;12.2.5.4.2.2.4 Method 4: Removal or Exchange of Alkoxy Groups;98
1.8.1.1.4.2.2.5;12.2.5.4.2.2.5 Method 5: Removal or Exchange of Amino or Nitro Groups;98
1.8.1.1.4.2.3;12.2.5.4.2.3 Of Carbon Functionalities;99
1.8.1.1.4.2.3.1;12.2.5.4.2.3.1 Method 1: Deacylation;99
1.8.1.1.4.2.3.2;12.2.5.4.2.3.2 Method 2: Decarboxylation;99
1.8.1.1.4.2.4;12.2.5.4.2.4 Modification of Substituents;100
1.8.1.1.4.2.4.1;12.2.5.4.2.4.1 Method 1: Modification of Carbonyl Groups;100
1.8.1.1.4.2.4.2;12.2.5.4.2.4.2 Method 2: Modification of Hydroxy Groups;100
1.8.1.1.4.2.4.3;12.2.5.4.2.4.3 Method 3: Modification of Nitro Groups;101
1.8.1.1.4.2.5;12.2.5.4.2.5 Rearrangement Reactions;101
1.8.1.1.4.2.5.1;12.2.5.4.2.5.1 Method 1: Rearrangement of 2H-Indazoles to 1H-Indazoles;101
1.8.1.1.4.2.5.2;12.2.5.4.2.5.2 Method 2: Rearrangement of Oxazino[3,2-b]indazoles by Nucleophilic Ring Opening;101
1.8.1.1.4.2.5.3;12.2.5.4.2.5.3 Method 3: Rearrangements of 3,4-Dihydropyrazino[1,2-b]indazol-2-ium 6-Oxides;102
1.9;Volume 15: Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom;108
1.9.1;15.7 Product Class 7: Quinolizinium Salts and Benzo Analogues;108
1.9.1.1;15.7.5 Quinolizinium Salts and Benzo Analogues;108
1.9.1.1.1;15.7.5.1 Quinolizinium Salts;108
1.9.1.1.1.1;15.7.5.1.1 Synthesis by Ring-Closure Reactions;108
1.9.1.1.1.1.1;15.7.5.1.1.1 By Annulation to an Arene;108
1.9.1.1.1.1.1.1;15.7.5.1.1.1.1 By Formation of Two C--C Bonds;108
1.9.1.1.1.1.1.1.1;15.7.5.1.1.1.1.1 Method 1: Enyne–Allene Rearrangement of 1-[3-(2-Alkynylphenyl)prop-2-ynyl]pyridinium Derivatives;108
1.9.1.1.1.2;15.7.5.1.2 Aromatization;109
1.9.1.1.1.2.1;15.7.5.1.2.1 Method 1: Oxidation of 1,2-Dihydroquinolizinium Derivatives;109
1.9.1.1.1.3;15.7.5.1.3 Synthesis by Substituent Modification;112
1.9.1.1.1.3.1;15.7.5.1.3.1 Substitution of Existing Substituents;112
1.9.1.1.1.3.1.1;15.7.5.1.3.1.1 Of Heteroatoms;112
1.9.1.1.1.3.1.1.1;15.7.5.1.3.1.1.1 Method 1: Stille Coupling of Bromoquinolizinium Derivatives;112
1.9.1.1.1.3.1.1.2;15.7.5.1.3.1.1.2 Method 2: Suzuki–Miyaura Coupling of Bromoquinolizinium Derivatives;114
1.9.1.1.1.3.1.1.3;15.7.5.1.3.1.1.3 Method 3: Sonogashira Coupling of Bromoquinolizinium Derivatives;115
1.9.1.1.2;15.7.5.2 Benzo[b]quinolizinium Salts;117
1.9.1.1.2.1;15.7.5.2.1 Synthesis by Ring-Closure Reactions;117
1.9.1.1.2.1.1;15.7.5.2.1.1 By Annulation to an Arene;117
1.9.1.1.2.1.1.1;15.7.5.2.1.1.1 By Formation of One C--C Bond;117
1.9.1.1.2.1.1.1.1;15.7.5.2.1.1.1.1 Method 1: Cyclization of 1-Benzyl-2-(1-hydroxy-1-methoxymethyl)pyridinium Derivatives;117
1.9.1.1.2.2;15.7.5.2.2 Synthesis by Substituent Modification;118
1.9.1.1.2.2.1;15.7.5.2.2.1 Substitution of Existing Substituents;118
1.9.1.1.2.2.1.1;15.7.5.2.2.1.1 Of Heteroatoms;118
1.9.1.1.2.2.1.1.1;15.7.5.2.2.1.1.1 Method 1: Suzuki–Miyaura Coupling of Benzo[b]quinoliziniumboronic Acids;118
1.9.1.1.2.2.1.1.2;15.7.5.2.2.1.1.2 Method 2: Replacement of Halogen Atoms by Nucleophilic Substitution;119
1.9.1.1.3;15.7.5.3 Benzo[c]quinolizinium Salts;121
1.9.1.1.3.1;15.7.5.3.1 Synthesis by Ring-Closure Reactions;121
1.9.1.1.3.1.1;15.7.5.3.1.1 By Annulation to an Arene;121
1.9.1.1.3.1.1.1;15.7.5.3.1.1.1 By Formation of One N--C Bond;121
1.9.1.1.3.1.1.1.1;15.7.5.3.1.1.1.1 Method 1: Cyclization of 2-[2-(2-Halophenyl)vinyl]pyridine Derivatives;121
1.9.1.1.4;15.7.5.4 Benzo[a]quinolizinium Salts;123
1.9.1.1.4.1;15.7.5.4.1 Synthesis by Ring-Closure Reactions;123
1.9.1.1.4.1.1;15.7.5.4.1.1 By Annulation to an Arene;123
1.9.1.1.4.1.1.1;15.7.5.4.1.1.1 By Formation of One C--C Bond;123
1.9.1.1.4.1.1.1.1;15.7.5.4.1.1.1.1 Method 1: Ring-Closing Metathesis of 1-Vinyl-2-(2-vinylphenyl)pyridinium Derivatives;123
1.10;Volume 16: Six-Membered Hetarenes with Two Identical Heteroatoms;126
1.10.1;16.5 Product Class 5: 1,2-Diselenins;126
1.10.1.1;16.5.2 1,2-Diselenins;126
1.10.1.1.1;16.5.2.1 Synthesis by Ring-Closure Reactions;127
1.10.1.1.1.1;16.5.2.1.1 By Formation of One Se--Se and Two Se--C Bonds;127
1.10.1.1.1.1.1;16.5.2.1.1.1 Fragment C--C--C--C and Two Se Fragments;127
1.10.1.1.1.1.1.1;16.5.2.1.1.1.1 Method 1: Selenation of an Organolithium Compound with Elemental Selenium;127
1.10.1.1.1.1.1.2;16.5.2.1.1.1.2 Method 2: Selenium Transfer from Selenous Acid to Benzyl Halides Using Tin(II) Chloride and Copper(II) Chloride;127
1.10.1.1.1.1.1.3;16.5.2.1.1.1.3 Method 3: Synthesis from 1,4-Bis(2-haloaryl)- or 1,4-Bis(2-halohetaryl)buta-1,3-diynes via Triple Cyclization;128
1.10.2;16.6 Product Class 6: 1,4-Diselenins;132
1.10.2.1;16.6.4 1,4-Diselenins;132
1.10.2.1.1;16.6.4.1 Synthesis by Ring-Closure Reactions;132
1.10.2.1.1.1;16.6.4.1.1 By Formation of Two Se--C Bonds;132
1.10.2.1.1.1.1;16.6.4.1.1.1 Fragments Se--C--C--Se and C--C;132
1.10.2.1.1.1.1.1;16.6.4.1.1.1.1 Method 1: Thermolysis of (Z)-1,2-Bis(benzylselanyl)ethene;132
1.10.2.1.1.1.1.2;16.6.4.1.1.1.2 Method 2: Cyclization of 3,4-Disubstituted Cyclobutene-1,2-diones;133
1.10.2.1.1.1.2;16.6.4.1.1.2 Fragments C--C--Se and C--C--Se;133
1.10.2.1.1.1.2.1;16.6.4.1.1.2.1 Method 1: Thermolysis of Selenadiazoles;133
1.10.2.1.1.1.2.2;16.6.4.1.1.2.2 Method 2: Photolysis of Dibenzo[c,g][1,2,5,6]tetraselenocins;134
1.10.3;16.12 Product Class 12: Pyrimidines;136
1.10.3.1;16.12.1 Synthesis by Ring-Closure Reactions;144
1.10.3.1.1;16.12.1.1 By Formation of Four N--C Bonds and One C--C Bond;144
1.10.3.1.1.1;16.12.1.1.1 Fragments C--C, N, N, C, and C;144
1.10.3.1.1.1.1;16.12.1.1.1.1 Method 1: Reaction of Alkyl Ketones with Orthoformates and Ammonia;144
1.10.3.1.1.1.2;16.12.1.1.1.2 Method 2: Reaction of 1-(2-Oxoethyl)pyridinium Bromides with 4-Nitrobenzaldehyde and Ammonia;145
1.10.3.1.2;16.12.1.2 By Formation of Four N--C Bonds;145
1.10.3.1.2.1;16.12.1.2.1 Fragments C--C--C, N, N, and C;145
1.10.3.1.2.1.1;16.12.1.2.1.1 Method 1: Reaction of ß-Dicarbonyl Derivatives with Aldehydes and Ammonia;145
1.10.3.1.2.1.2;16.12.1.2.1.2 Method 2: Reaction of (Perfluoroalkyl)acetaldehydes with Ammonia and Aldehydes;146
1.10.3.1.2.1.3;16.12.1.2.1.3 Method 3: Reaction of ß-Dicarbonyl Derivatives with Ortho Esters;147
1.10.3.1.3;16.12.1.3 By Formation of Three N--C Bonds and One C--C Bond;148
1.10.3.1.3.1;16.12.1.3.1 Fragments N--C--C, N, C, C;148
1.10.3.1.3.1.1;16.12.1.3.1.1 Method 1: Reaction of Vinylamines with Orthoformates and Ammonia;148
1.10.3.1.3.2;16.12.1.3.2 Fragments N--C, C--C, N, and C;150
1.10.3.1.3.2.1;16.12.1.3.2.1 Method 1: Reaction of Aryl Methyl Ketones with Aryl Aldehydes, Aryl Cyanides, and Hydroxylamine;150
1.10.3.1.4;16.12.1.4 By Formation of Two N--C Bonds and Two C--C Bonds;150
1.10.3.1.4.1;16.12.1.4.1 Fragments N--C--N, C, C, and C;150
1.10.3.1.4.1.1;16.12.1.4.1.1 Method 1: One-Pot Reaction of Aryl Cyanides with Alkylphosphonates, Aromatic Aldehydes, and Amidines;150
1.10.3.1.5;16.12.1.5 By Formation of Three N--C Bonds;151
1.10.3.1.5.1;16.12.1.5.1 Fragments N--C--C--C, N, and C;151
1.10.3.1.5.1.1;16.12.1.5.1.1 Method 1: Reaction of 2-(Aminomethyl)acrylates with Formamide;151
1.10.3.1.5.2;16.12.1.5.2 Fragments C--C--C, N--C, and N;152
1.10.3.1.5.2.1;16.12.1.5.2.1 Method 1: Reaction of ß-Dicarbonyl Derivatives with Formamide;152
1.10.3.1.5.2.1.1;16.12.1.5.2.1.1 Variation 1: Reaction of 1,3-Diketones;152
1.10.3.1.5.2.1.2;16.12.1.5.2.1.2 Variation 2: Reaction of 4,4-Dimethoxybutan-2-one;153
1.10.3.1.5.2.1.3;16.12.1.5.2.1.3 Variation 3: Reaction of Malonaldehyde Diacetals;153
1.10.3.1.5.2.1.4;16.12.1.5.2.1.4 Variation 4: Reaction of 3-Heterosubstituted Propenals or Propenones;154
1.10.3.1.5.2.2;16.12.1.5.2.2 Method 2: Reaction of Malonyl Chlorides with Nitriles;155
1.10.3.1.5.2.3;16.12.1.5.2.3 Method 3: Reaction of ß-Diketones with Cyanamide;156
1.10.3.1.6;16.12.1.6 By Formation of Two N--C Bonds and One C--C Bond;157
1.10.3.1.6.1;16.12.1.6.1 Fragments N--C, N--C, and C--C;157
1.10.3.1.6.1.1;16.12.1.6.1.1 Method 1: Trimerization of Nitriles;157
1.10.3.1.6.1.2;16.12.1.6.1.2 Method 2: Reaction of Alkynes with Nitriles;158
1.10.3.1.6.1.3;16.12.1.6.1.3 Method 3: Reaction of Alkyne Precursors with Nitriles;160
1.10.3.1.6.1.3.1;16.12.1.6.1.3.1 Variation 1: Reaction of Carbonyl Compounds Activated with Trifluoromethanesulfonic Anhydride;160
1.10.3.1.6.1.3.2;16.12.1.6.1.3.2 Variation 2: Reaction of Ketimines;162
1.10.3.1.6.1.3.3;16.12.1.6.1.3.3 Variation 3: Reaction of Enol Trifluoromethanesulfonates;163
1.10.3.1.6.1.3.4;16.12.1.6.1.3.4 Variation 4: Reaction of Heterosubstituted Alkenes;163
1.10.3.1.6.1.3.5;16.12.1.6.1.3.5 Variation 5: Reaction of 1,1-Diethoxybut-2-ene;164
1.10.3.1.6.1.4;16.12.1.6.1.4 Method 4: Reaction of Diethyl Malonate with Trifluoroacetonitrile;165
1.10.3.1.6.1.5;16.12.1.6.1.5 Method 5: Reaction of C--H Acidic Compounds with Formamide and Equivalents;165
1.10.3.1.6.1.5.1;16.12.1.6.1.5.1 Variation 1: Reaction of Phenylacetonitrile;166
1.10.3.1.6.1.5.2;16.12.1.6.1.5.2 Variation 2: Reaction of Malononitrile and Dimethyl Malonate;166
1.10.3.1.6.1.5.3;16.12.1.6.1.5.3 Variation 3: Reaction of Ketones;167
1.10.3.1.6.1.6;16.12.1.6.1.6 Method 6: Reaction of Acetonitriles with Aryl Cyanates;168
1.10.3.1.6.2;16.12.1.6.2 Fragments N--C--C, N--C, and C;169
1.10.3.1.6.2.1;16.12.1.6.2.1 Method 1: Reaction of Acetonitriles with Phosgene;169
1.10.3.1.6.2.2;16.12.1.6.2.2 Method 2: Reaction of Acetonitriles with (Trichloromethyl)benzene;170
1.10.3.1.6.3;16.12.1.6.3 Fragments C--N--C, C--C, and N;170
1.10.3.1.6.3.1;16.12.1.6.3.1 Method 1: Reaction of Vinylamines with Benzoyl Isocyanate;170
1.10.3.1.6.4;16.12.1.6.4 Fragments N--C--N, C--C, and C;171
1.10.3.1.6.4.1;16.12.1.6.4.1 Method 1: Reaction of Cyanoacetates and Aromatic Aldehydes with Amidine Derivatives;171
1.10.3.1.6.4.1.1;16.12.1.6.4.1.1 Variation 1: Reaction with Guanidine;171
1.10.3.1.6.4.1.2;16.12.1.6.4.1.2 Variation 2: Reaction with a Polymer-Bound Thiouronium Salt;172
1.10.3.1.6.4.2;16.12.1.6.4.2 Method 2: Reaction of Malononitrile and Aromatic Aldehydes with Amidine Derivatives;173
1.10.3.1.6.4.3;16.12.1.6.4.3 Method 3: Reaction of Malononitrile with Carbon Disulfide, an S-Alkylisothiouronium Salt, and an Alkylating Agent;174
1.10.3.1.6.4.4;16.12.1.6.4.4 Method 4: Reaction of a Substituted Acetate with Ethyl Formate and Guanidine;174
1.10.3.1.6.4.5;16.12.1.6.4.5 Method 5: Reaction of Aryl Methyl Ketones with Benzaldehydes and Acetimidamide;175
1.10.3.1.6.4.6;16.12.1.6.4.6 Method 6: Reaction of Aroylacetonitriles with Guanidines and Activated Formates;176
1.10.3.1.6.4.7;16.12.1.6.4.7 Method 7: Reaction of Amidines with Alkynes and a One-Carbon Fragment;177
1.10.3.1.6.4.7.1;16.12.1.6.4.7.1 Variation 1: Reaction of tert-Butyl Isocyanide with Alkynes and Amidines;177
1.10.3.1.6.4.7.2;16.12.1.6.4.7.2 Variation 2: Reaction of Acid Chlorides with Alkynes and Amidines;178
1.10.3.1.6.4.7.3;16.12.1.6.4.7.3 Variation 3: Reaction of Hexacarbonylmolybdenum(0) with Alkynes, Amidines, and Iodobenzene;179
1.10.3.1.7;16.12.1.7 By Formation of Two N--C Bonds;179
1.10.3.1.7.1;16.12.1.7.1 Fragments N--C--C--C--N and C;179
1.10.3.1.7.1.1;16.12.1.7.1.1 Method 1: Reaction of Malonamides with Ethyl Formate;180
1.10.3.1.7.1.2;16.12.1.7.1.2 Method 2: Reaction of Amidinoacetamides with Formamide;180
1.10.3.1.7.1.3;16.12.1.7.1.3 Method 3: Reaction of Malonimidic Acid Esters with Acid Chlorides;181
1.10.3.1.7.1.4;16.12.1.7.1.4 Method 4: Reaction of Malonimidamides with Esters;182
1.10.3.1.7.1.5;16.12.1.7.1.5 Method 5: Reaction of 3-Aminoacrylamides with Acid Derivatives;182
1.10.3.1.7.1.6;16.12.1.7.1.6 Method 6: Reaction of 3-Amino-2-cyanoacrylamides with Anhydrides;183
1.10.3.1.7.1.7;16.12.1.7.1.7 Method 7: Reaction of 4-Amino-1-azabutadiene and Dimethylformamide;184
1.10.3.1.7.2;16.12.1.7.2 Fragments C--C--C--N--C and N;184
1.10.3.1.7.2.1;16.12.1.7.2.1 Method 1: Reaction of N-Acylacrylamides with Ammonia;184
1.10.3.1.7.2.2;16.12.1.7.2.2 Method 2: Reaction of N,2-Diacylvinylamines with Ammonia and Derivatives;185
1.10.3.1.7.2.2.1;16.12.1.7.2.2.1 Variation 1: Reaction with Ammonium Salts;186
1.10.3.1.7.2.2.2;16.12.1.7.2.2.2 Variation 2: Reaction with Formamide;186
1.10.3.1.7.2.2.3;16.12.1.7.2.2.3 Variation 3: Reaction with Urea;187
1.10.3.1.7.3;16.12.1.7.3 Fragments C--C--C--N and N--C;188
1.10.3.1.7.3.1;16.12.1.7.3.1 Method 1: Reaction of 3-Chloroacrylonitriles with Nitriles;188
1.10.3.1.7.3.2;16.12.1.7.3.2 Method 2: Reaction of 3,3-Bis(methylsulfanyl)acrylonitrile with Amides;189
1.10.3.1.7.3.3;16.12.1.7.3.3 Method 3: Reaction of 3-Aminoacrylates;190
1.10.3.1.7.3.3.1;16.12.1.7.3.3.1 Variation 1: With Amides;190
1.10.3.1.7.3.3.2;16.12.1.7.3.3.2 Variation 2: With Benzimidates;191
1.10.3.1.7.3.3.3;16.12.1.7.3.3.3 Variation 3: With Nitriles;191
1.10.3.1.7.3.4;16.12.1.7.3.4 Method 4: Reaction of 3-Aminoprop-2-en-1-ones with Nitriles;191
1.10.3.1.7.3.5;16.12.1.7.3.5 Method 5: Reaction of 1,3-Diketimines with Benzonitrile;192
1.10.3.1.7.3.6;16.12.1.7.3.6 Method 6: Reaction of 3-Aminopropenals with Formamide;193
1.10.3.1.7.3.7;16.12.1.7.3.7 Method 7: Reaction of 3-Aminoacrylonitriles with Nitriles;194
1.10.3.1.7.4;16.12.1.7.4 Fragments N--C--N and C--C--C;194
1.10.3.1.7.4.1;16.12.1.7.4.1 Method 1: Reaction of Vinamidinium Salts with Amidine Derivatives;194
1.10.3.1.7.4.2;16.12.1.7.4.2 Method 2: Reaction of Malonates with Amidine Derivatives;196
1.10.3.1.7.4.3;16.12.1.7.4.3 Method 3: Reaction of Cyanoacetates (a-Cyanocarboxylates) with Amidine Derivatives;197
1.10.3.1.7.4.4;16.12.1.7.4.4 Method 4: Reaction of 3,3-Diheterosubstituted Acrylates with Amidine Derivatives;198
1.10.3.1.7.4.4.1;16.12.1.7.4.4.1 Variation 1: Reaction of 3,3-Dialkoxyacrylates with Amidine Derivatives;198
1.10.3.1.7.4.4.2;16.12.1.7.4.4.2 Variation 2: Reaction of 3,3-Bis(methylsulfanyl)acrylates with Amidine Derivatives;198
1.10.3.1.7.4.4.3;16.12.1.7.4.4.3 Variation 3: Reaction of 3-Amino-3-(methylsulfanyl)acrylates with Guanidine or Thiourea;199
1.10.3.1.7.4.5;16.12.1.7.4.5 Method 5: Reaction of a-Formyl Esters or Equivalents with Amidine Derivatives;199
1.10.3.1.7.4.6;16.12.1.7.4.6 Method 6: Reaction of ß-Oxo Esters with Amidine Derivatives;201
1.10.3.1.7.4.7;16.12.1.7.4.7 Method 7: Reaction of 3-Heterosubstituted Acrylates with Amidine Derivatives;204
1.10.3.1.7.4.8;16.12.1.7.4.8 Method 8: Reaction of Alkynyl or Allenyl Esters with Amidine Derivatives;207
1.10.3.1.7.4.9;16.12.1.7.4.9 Method 9: Reaction of 3-Unsubstituted, 3-Alkyl-, and 3-Arylacrylates with Amidine Derivatives;208
1.10.3.1.7.4.10;16.12.1.7.4.10 Method 10: Reaction of Malononitriles with Amidine Derivatives;209
1.10.3.1.7.4.11;16.12.1.7.4.11 Method 11: Reaction of 3,3-Diheterosubstituted Acrylonitriles with Amidine Derivatives;210
1.10.3.1.7.4.11.1;16.12.1.7.4.11.1 Variation 1: Reaction of 3,3-Dialkoxyacrylonitriles;210
1.10.3.1.7.4.11.2;16.12.1.7.4.11.2 Variation 2: Reaction of 3,3-Bis(methylsulfanyl)acrylonitriles;211
1.10.3.1.7.4.12;16.12.1.7.4.12 Method 12: Reaction of 3-Heterosubstituted Acrylonitriles with Amidine Derivatives;212
1.10.3.1.7.4.12.1;16.12.1.7.4.12.1 Variation 1: Reaction of 3-Haloacrylonitriles;213
1.10.3.1.7.4.12.2;16.12.1.7.4.12.2 Variation 2: Reaction of 3-Alkoxyacrylonitriles;213
1.10.3.1.7.4.12.3;16.12.1.7.4.12.3 Variation 3: Reaction of 3-(Methylsulfanyl)acrylonitriles;215
1.10.3.1.7.4.12.4;16.12.1.7.4.12.4 Variation 4: Reaction of 3-Aminoacrylonitriles;216
1.10.3.1.7.4.13;16.12.1.7.4.13 Method 13: Reaction of Propynenitriles or Buta-2,3-dienenitriles with Amidine Derivatives;217
1.10.3.1.7.4.14;16.12.1.7.4.14 Method 14: Reaction of 3-Arylacrylonitriles with Amidine Derivatives;218
1.10.3.1.7.4.15;16.12.1.7.4.15 Method 15: Reaction of ß-Dialdehydes or Equivalents with Amidine Derivatives;220
1.10.3.1.7.4.15.1;16.12.1.7.4.15.1 Variation 1: Reaction of Malonaldehydes;220
1.10.3.1.7.4.15.2;16.12.1.7.4.15.2 Variation 2: Reaction of Sodium 3,3-Dimethoxy-2-(methoxycarbonyl)prop-1-en-1-olate;221
1.10.3.1.7.4.15.3;16.12.1.7.4.15.3 Variation 3: Reaction of Malonaldehyde Diacetals;221
1.10.3.1.7.4.15.4;16.12.1.7.4.15.4 Variation 4: Reaction of 3-Heterosubstituted Propenals;223
1.10.3.1.7.4.16;16.12.1.7.4.16 Method 16: Reaction of ß-Diketones with Amidine Derivatives;226
1.10.3.1.7.4.16.1;16.12.1.7.4.16.1 Variation 1: Reaction with Guanidines;226
1.10.3.1.7.4.16.2;16.12.1.7.4.16.2 Variation 2: Reaction with O-Methyluronium Salts;228
1.10.3.1.7.4.16.3;16.12.1.7.4.16.3 Variation 3: Reaction with Urea or Thiourea;228
1.10.3.1.7.4.16.4;16.12.1.7.4.16.4 Variation 4: Reaction with Arylamidines;229
1.10.3.1.7.4.17;16.12.1.7.4.17 Method 17: Reaction of 3,3-Dialkoxypropan-1-ones with Amidine Derivatives;230
1.10.3.1.7.4.18;16.12.1.7.4.18 Method 18: Reaction of 3,3-Diheterosubstituted Prop-2-en-1-ones with Amidine Derivatives;231
1.10.3.1.7.4.18.1;16.12.1.7.4.18.1 Variation 1: Reaction of 3,3-Dialkoxyprop-2-en-1-ones;231
1.10.3.1.7.4.18.2;16.12.1.7.4.18.2 Variation 2: Reaction of 3,3-Disulfanylprop-2-en-1-ones or 3-Amino-3-sulfanylprop-2-en-1-ones;231
1.10.3.1.7.4.18.3;16.12.1.7.4.18.3 Variation 3: Reaction of 3,3-Diaminoprop-2-en-1-ones;234
1.10.3.1.7.4.19;16.12.1.7.4.19 Method 19: Reaction of 3-Heterosubstituted Prop-2-en-1-ones with Amidine Derivatives;234
1.10.3.1.7.4.19.1;16.12.1.7.4.19.1 Variation 1: Reaction of 3-Haloprop-2-en-1-ones;234
1.10.3.1.7.4.19.2;16.12.1.7.4.19.2 Variation 2: Reaction of 3-Alkoxyprop-2-en-1-ones;235
1.10.3.1.7.4.19.3;16.12.1.7.4.19.3 Variation 3: Reaction of 3-Sulfanylprop-2-en-1-ones;238
1.10.3.1.7.4.19.4;16.12.1.7.4.19.4 Variation 4: Reaction of 3-Aminoprop-2-en-1-ones;238
1.10.3.1.7.4.20;16.12.1.7.4.20 Method 20: Reaction of Prop-2-yn-1-ones with Amidine Derivatives;240
1.10.3.1.7.4.21;16.12.1.7.4.21 Method 21: Reaction of 3-Arylprop-2-en-1-ones with Amidine Derivatives;243
1.10.3.1.7.4.22;16.12.1.7.4.22 Method 22: Reaction of 1-Amino-1-(benzotriazol-1-yl)-3,4,4-trichloro-2-nitrobuta-1,3-dienes with Amidine Derivatives;246
1.10.3.1.7.4.23;16.12.1.7.4.23 Method 23: Pyrimidines by Solid-Phase Synthesis;246
1.10.3.1.7.4.23.1;16.12.1.7.4.23.1 Variation 1: Reactions of Polymer-Supported Three-Carbon Fragments;246
1.10.3.1.7.4.23.2;16.12.1.7.4.23.2 Variation 2: Reactions of Polymer-Supported Amidine Derivatives;252
1.10.3.1.8;16.12.1.8 By Formation of One N--C and One C--C Bond;254
1.10.3.1.8.1;16.12.1.8.1 Fragments N--C--N--C--C and C;254
1.10.3.1.8.1.1;16.12.1.8.1.1 Method 1: Reaction of N-[2-(3-Methylisoxazol-5-yl)vinyl]amidines with Dimethylformamide Acetals;254
1.10.3.1.8.2;16.12.1.8.2 Fragments N--C--N--C and C--C;255
1.10.3.1.8.2.1;16.12.1.8.2.1 Method 1: Reaction of 3-Cyano-2-methylisothiourea or 2-Cyanoguanidines with Ketones;255
1.10.3.1.8.2.2;16.12.1.8.2.2 Method 2: Reaction of 1,3-Diazabuta-1,3-dienes with Alkynes;255
1.10.3.1.8.2.2.1;16.12.1.8.2.2.1 Variation 1: Reaction of 4,4-Bis(methylsulfanyl)-2-phenyl-1,3-diazabuta-1,3-diene;256
1.10.3.1.8.2.2.2;16.12.1.8.2.2.2 Variation 2: Reaction of 4-(Dimethylamino)-1,3-diazabuta-1,3-dienes;256
1.10.3.1.8.2.3;16.12.1.8.2.3 Method 3: Reaction of 4-(Dimethylamino)-2-(methylsulfanyl)-1,3-diazabuta-1,3-diene with Ketenes;257
1.10.3.1.8.3;16.12.1.8.3 Fragments C--C--N--C and N--C;258
1.10.3.1.8.3.1;16.12.1.8.3.1 Method 1: Reaction of Azapropenylium Perchlorates with 1,1,3,3-Tetramethylguanidine;258
1.10.3.1.8.3.2;16.12.1.8.3.2 Method 2: Reaction of 2-Azabuta-1,3-dienes with Nitriles;259
1.10.3.1.8.3.3;16.12.1.8.3.3 Method 3: Reaction of N-Vinylamides with Nitriles;261
1.10.3.1.8.3.4;16.12.1.8.3.4 Method 4: Reaction of Ethyl (Cyanoacetyl)carbamate with Trifluoroacetonitrile;262
1.10.3.1.8.3.5;16.12.1.8.3.5 Method 5: Dimerization of N-Cyanothioacetimidates;263
1.10.3.1.8.4;16.12.1.8.4 Fragments N--C--C and C--N--C;263
1.10.3.1.8.4.1;16.12.1.8.4.1 Method 1: Reaction of Acetonitriles with N-(Dichloromethylene)trichloromethanamine;263
1.10.3.1.8.4.2;16.12.1.8.4.2 Method 2: Reaction of Cyanothioacetamide with Benzoyl Isothiocyanate;264
1.10.3.1.8.4.3;16.12.1.8.4.3 Method 3: Reaction of Acetamides with N-Cyanoimidates or N-Acylimidates;264
1.10.3.1.8.4.4;16.12.1.8.4.4 Method 4: Reaction of Enamines with N-(Dichloromethylene)trichloromethanamine;266
1.10.3.1.8.4.5;16.12.1.8.4.5 Method 5: Reaction of Enamines with Acyl Isothiocyanates;267
1.10.3.1.8.4.6;16.12.1.8.4.6 Method 6: Reaction of Enamines with N-[Bis(methylsulfanyl)methylene]cyanamide;268
1.10.3.1.8.4.7;16.12.1.8.4.7 Method 7: Reaction of a-Halo Oxime Derivatives with Grignard Reagents;268
1.10.3.1.9;16.12.1.9 By Formation of One N--C Bond;270
1.10.3.1.9.1;16.12.1.9.1 Fragment N--C--C--C--N--C;270
1.10.3.1.9.1.1;16.12.1.9.1.1 Method 1: Cyclization of 3-(Acylamino)but-2-enamides;270
1.10.3.1.9.1.2;16.12.1.9.1.2 Method 2: Cyclization of 3-Amino-N-acylthioacrylamides;270
1.10.3.1.9.1.3;16.12.1.9.1.3 Method 3: Cyclization of 3-Amino-N-cyano-3-methoxyacrylimidate;271
1.10.3.1.9.1.4;16.12.1.9.1.4 Method 4: Cyclization of 3-(Acylamino)-2-cyanoacrylates and 2-Cyano-3-(thioacylamino)acrylates;272
1.10.3.1.9.1.5;16.12.1.9.1.5 Method 5: Cyclization of N-(2-Cyanovinyl)amidines;275
1.10.3.1.9.1.6;16.12.1.9.1.6 Method 6: Cyclization of 1-(Dimethylamino)-5-(dimethylimino)-2-azapenta-1,3-dienes;275
1.10.3.1.9.1.7;16.12.1.9.1.7 Method 7: Cyclization of 3-(Vinylamino)but-2-enamides;276
1.10.3.1.9.2;16.12.1.9.2 Fragment N--C--N--C--C--C;276
1.10.3.1.9.2.1;16.12.1.9.2.1 Method 1: Cyclization of N-(3-Substituted Acryloyl)ureas;276
1.10.3.1.9.2.2;16.12.1.9.2.2 Method 2: Cyclization of 3-Ureidoacrylates;278
1.10.3.1.9.2.3;16.12.1.9.2.3 Method 3: Cyclization of N-[2-(Methoxycarbonyl)ethylidene]ureas;280
1.10.3.1.9.2.4;16.12.1.9.2.4 Method 4: Cyclization of 3-Ureidoacrylonitriles;281
1.10.3.1.9.2.5;16.12.1.9.2.5 Method 5: Cyclization of N-(2-Cyanovinyl)imidamides;282
1.10.3.1.9.2.6;16.12.1.9.2.6 Method 6: Cyclization of 1-(Cyanoacetyl)-2-methylisoureas;283
1.10.3.1.9.2.7;16.12.1.9.2.7 Method 7: Cyclization of 3-(Cyanoamino)acrylonitriles;284
1.10.3.1.9.2.8;16.12.1.9.2.8 Method 8: Cyclization of (Cyanoacetyl)cyanamides and Equivalents;284
1.10.3.1.10;16.12.1.10 By Formation of One C--C Bond;287
1.10.3.1.10.1;16.12.1.10.1 Fragment C--C--N--C--N--C;287
1.10.3.1.10.1.1;16.12.1.10.1.1 Method 1: Cyclization of 1-Acetyl-3-cyanourea;288
1.10.3.1.10.1.2;16.12.1.10.1.2 Method 2: Cyclization of N2-Carbamoyl-N1-vinylbenzimidamides;288
1.10.3.2;16.12.2 Synthesis by Ring Transformation;289
1.10.3.2.1;16.12.2.1 By Ring Enlargement;289
1.10.3.2.1.1;16.12.2.1.1 Of Three-Membered Carbocycles;289
1.10.3.2.1.1.1;16.12.2.1.1.1 Method 1: Reaction of Cyclopropenones with Amidoximes;289
1.10.3.2.1.2;16.12.2.1.2 Of Four-Membered Heterocycles;290
1.10.3.2.1.2.1;16.12.2.1.2.1 Method 1: Reaction of Azetes with Nitriles;290
1.10.3.2.1.2.2;16.12.2.1.2.2 Method 2: Reaction of Azetidinones with Imidates;290
1.10.3.2.1.3;16.12.2.1.3 Of Five-Membered Heterocycles;291
1.10.3.2.1.3.1;16.12.2.1.3.1 Method 1: Reaction of Furans;291
1.10.3.2.1.3.2;16.12.2.1.3.2 Method 2: Reaction of 3-Acyl-2-oxotetrahydrothiophene with Amidine Derivatives;293
1.10.3.2.1.3.3;16.12.2.1.3.3 Method 3: Reaction of 2,3,4,5-Tetraphenylpyrrole with Sulfenamides;294
1.10.3.2.1.3.4;16.12.2.1.3.4 Method 4: Reaction of Isoxazoles;295
1.10.3.2.1.3.4.1;16.12.2.1.3.4.1 Variation 1: Rearrangement of 5-(Acylamino)isoxazoles;295
1.10.3.2.1.3.4.2;16.12.2.1.3.4.2 Variation 2: Rearrangement of N-(Isoxazol-4-ylcarbonyl)ureas and N1-(Isoxazol-4-ylcarbonyl)benzimidamides;296
1.10.3.2.1.3.5;16.12.2.1.3.5 Method 5: Reaction of Oxazoles;297
1.10.3.2.1.3.6;16.12.2.1.3.6 Method 6: Reaction of Pyrazoles;298
1.10.3.2.1.3.7;16.12.2.1.3.7 Method 7: Reaction of Imidazoles;299
1.10.3.2.1.3.7.1;16.12.2.1.3.7.1 Variation 1: Reaction with Chloroform;299
1.10.3.2.1.3.7.2;16.12.2.1.3.7.2 Variation 2: Rearrangement of 1-Benzoyldihydroimidazoles;300
1.10.3.2.1.3.7.3;16.12.2.1.3.7.3 Variation 3: Rearrangement of 4-(Chloromethyl)dihydroimidazoles;300
1.10.3.2.1.3.7.4;16.12.2.1.3.7.4 Variation 4: Rearrangement of Methyleneimidazolidin-4-ones;302
1.10.3.2.1.3.7.5;16.12.2.1.3.7.5 Variation 5: Reaction with Acetylenes;302
1.10.3.2.1.3.7.6;16.12.2.1.3.7.6 Variation 6: Reaction with Phenylmalonaldehyde;303
1.10.3.2.1.3.8;16.12.2.1.3.8 Method 8: Reaction of 1,2,4-Oxadiazoles;304
1.10.3.2.1.3.8.1;16.12.2.1.3.8.1 Variation 1: Hydrogenation of 3-[(3-Oxoprop-1-enyl)amino)]-1,2,4-oxadiazoles;304
1.10.3.2.1.3.8.2;16.12.2.1.3.8.2 Variation 2: Reaction of 3-Amino-5-methyl-1,2,4-oxadiazole with ß-Diketones;304
1.10.3.2.1.3.9;16.12.2.1.3.9 Method 9: Reaction of 1,2,4-Dithiazolium Salts with Nitrogen-Containing Derivatives of Carboxylic Acids;305
1.10.3.2.2;16.12.2.2 Formal Exchange of Ring Members with Retention of the Ring Size;306
1.10.3.2.2.1;16.12.2.2.1 Method 1: Reaction of Pyran-2-ones with Amidine Derivatives;307
1.10.3.2.2.1.1;16.12.2.2.1.1 Variation 1: Use of Two-Carbon Ring Fragments;307
1.10.3.2.2.1.2;16.12.2.2.1.2 Variation 2: Use of Three-Carbon Ring Fragments;309
1.10.3.2.2.2;16.12.2.2.2 Method 2: Reaction of Pyran-4-ones with Amidine Derivatives;310
1.10.3.2.2.3;16.12.2.2.3 Method 3: Reaction of 1,3-Oxazines;314
1.10.3.2.2.3.1;16.12.2.2.3.1 Variation 1: Reaction of 1,3-Oxazin-4-ones with Ammonia;314
1.10.3.2.2.3.2;16.12.2.2.3.2 Variation 2: Rearrangement of 2-Amino-1,3-oxazin-4-ones;315
1.10.3.2.2.3.3;16.12.2.2.3.3 Variation 3: Reaction of 1,3-Oxazin-4-ones with Thioamides;315
1.10.3.2.2.3.4;16.12.2.2.3.4 Variation 4: Reaction of 1,3-Oxazin-6-ones with Ammonia;316
1.10.3.2.2.3.5;16.12.2.2.3.5 Variation 5: Rearrangement of 1,3-Oxazine-5-carboxamides;317
1.10.3.2.2.3.6;16.12.2.2.3.6 Variation 6: Reaction of 1,3-Oxazinium Perchlorates with Ammonia;317
1.10.3.2.2.4;16.12.2.2.4 Method 4: Reaction of 1,3-Thiazinones or 1,4-Benzothiazines;318
1.10.3.2.2.5;16.12.2.2.5 Method 5: Reaction of Pyrimidinones and Pyrimidinecarboxylates;320
1.10.3.2.2.6;16.12.2.2.6 Method 6: Ring Opening of Polycycles with Retention of the Pyrimidine Ring;321
1.10.3.2.2.7;16.12.2.2.7 Method 7: Rearrangement of 1,2,4-Oxadiazines;323
1.10.3.2.2.8;16.12.2.2.8 Method 8: Reaction of 1,3,5-Oxadiazinium or 1,3,5-Thiadiazinium Salts with Active Methylene Compounds;323
1.10.3.2.2.9;16.12.2.2.9 Method 9: Reaction of 1,2,4-Triazines with N,N-Diethylprop-1-ynamine;325
1.10.3.2.2.10;16.12.2.2.10 Method 10: Reaction of 1,3,5-Triazines;326
1.10.3.2.2.10.1;16.12.2.2.10.1 Variation 1: Reaction of 1,3,5-Triazines with Dienophiles;326
1.10.3.2.2.10.2;16.12.2.2.10.2 Variation 2: Reaction of 1,3,5-Triazines with Active Methylene Compounds;329
1.10.3.2.2.10.3;16.12.2.2.10.3 Variation 3: Rearrangement of 2-(Acylmethyl)-1,3,5-triazines;330
1.10.3.2.2.10.4;16.12.2.2.10.4 Variation 4: Thermolysis of 2-Alkyl-1,2-dihydro-1,3,5-triazines;331
1.10.3.2.2.10.5;16.12.2.2.10.5 Variation 5: Reaction of 1,3,5-Triazinediones;331
1.10.3.2.2.11;16.12.2.2.11 Method 11: Reaction of 1,2,3,5-Oxathiadiazine 2,2-Dioxides with Active Methylene Compounds;332
1.10.3.2.3;16.12.2.3 By Ring Contraction;333
1.10.3.2.3.1;16.12.2.3.1 Method 1: Ring Contraction of 1,4-Diazepines;333
1.10.3.3;16.12.3 Aromatization;333
1.10.3.3.1;16.12.3.1 By Oxidation;333
1.10.3.3.1.1;16.12.3.1.1 Method 1: Dehydrogenation of Dihydropyrimidines;333
1.10.3.3.1.2;16.12.3.1.2 Method 2: Dehydrogenation of Tetrahydropyrimidines;335
1.10.3.3.1.3;16.12.3.1.3 Method 3: Pyrimidinones by Dehydrogenation;336
1.10.3.3.1.4;16.12.3.1.4 Method 4: Oxidation of 6-Methyl-3,4-dihydropyrimidin-2(1H)-ones;339
1.10.3.3.2;16.12.3.2 By Elimination;340
1.10.3.3.2.1;16.12.3.2.1 Method 1: Acid-Catalyzed Elimination of Water;340
1.10.3.3.2.2;16.12.3.2.2 Method 2: Base-Catalyzed Elimination of HX;341
1.10.3.4;16.12.4 Synthesis by Substituent Modification;343
1.10.3.4.1;16.12.4.1 Substitution of Existing Substituents;343
1.10.3.4.1.1;16.12.4.1.1 Of Hydrogen;343
1.10.3.4.1.1.1;16.12.4.1.1.1 Method 1: Hydrogen/Deuterium Exchange;343
1.10.3.4.1.1.2;16.12.4.1.1.2 Method 2: Metalation;344
1.10.3.4.1.1.3;16.12.4.1.1.3 Method 3: Silylation;349
1.10.3.4.1.1.4;16.12.4.1.1.4 Method 4: C-Acylation;350
1.10.3.4.1.1.4.1;16.12.4.1.1.4.1 Variation 1: Formylation;350
1.10.3.4.1.1.4.2;16.12.4.1.1.4.2 Variation 2: Acylation by Radicals;351
1.10.3.4.1.1.4.3;16.12.4.1.1.4.3 Variation 3: Carboxylation;352
1.10.3.4.1.1.4.4;16.12.4.1.1.4.4 Variation 4: Carbamoylation;353
1.10.3.4.1.1.5;16.12.4.1.1.5 Method 5: Cyanation;354
1.10.3.4.1.1.6;16.12.4.1.1.6 Method 6: Hydroxyalkylation and Related Reactions;355
1.10.3.4.1.1.7;16.12.4.1.1.7 Method 7: C-Alkylation;356
1.10.3.4.1.1.8;16.12.4.1.1.8 Method 8: C-Arylation;360
1.10.3.4.1.1.9;16.12.4.1.1.9 Method 9: Halogenation;364
1.10.3.4.1.1.10;16.12.4.1.1.10 Method 10: Hydroxylation;367
1.10.3.4.1.1.11;16.12.4.1.1.11 Method 11: Nitration;368
1.10.3.4.1.1.12;16.12.4.1.1.12 Method 12: Nitrosation;369
1.10.3.4.1.1.13;16.12.4.1.1.13 Method 13: Amination;370
1.10.3.4.1.2;16.12.4.1.2 Of Metals;373
1.10.3.4.1.2.1;16.12.4.1.2.1 Method 1: Reaction of (Trialkylstannyl)pyrimidines with Aryl Halides or Acid Chlorides;373
1.10.3.4.1.2.2;16.12.4.1.2.2 Method 2: Reaction of Pyrimidin-5-ylboronic Acids or (Pyrimidin-5-yl)trifluoroborates with Hetaryl Halides;376
1.10.3.4.1.3;16.12.4.1.3 Of Carbon Functionalities;380
1.10.3.4.1.3.1;16.12.4.1.3.1 Method 1: Decarboxylation;380
1.10.3.4.1.3.2;16.12.4.1.3.2 Method 2: N-Deacylation;381
1.10.3.4.1.3.3;16.12.4.1.3.3 Method 3: N-Dealkylation;382
1.10.3.4.1.3.4;16.12.4.1.3.4 Method 4: Removal of Protecting Groups;382
1.10.3.4.1.3.4.1;16.12.4.1.3.4.1 Variation 1: Benzyloxymethyl Group;382
1.10.3.4.1.3.4.2;16.12.4.1.3.4.2 Variation 2: Cyanoethyl Group;383
1.10.3.4.1.3.4.3;16.12.4.1.3.4.3 Variation 3: Benzyl Group;384
1.10.3.4.1.3.5;16.12.4.1.3.5 Method 5: Conversion of Pyrimidine-5-carbaldehydes into 5-Hydroxypyrimidines;385
1.10.3.4.1.4;16.12.4.1.4 Of Heteroatoms;385
1.10.3.4.1.4.1;16.12.4.1.4.1 Dehalogenation;385
1.10.3.4.1.4.1.1;16.12.4.1.4.1.1 Method 1: Dehalogenation with Palladium on Carbon;386
1.10.3.4.1.4.1.2;16.12.4.1.4.1.2 Method 2: Dechlorination by Zinc Dust;387
1.10.3.4.1.4.1.3;16.12.4.1.4.1.3 Method 3: Dechlorination of 3-Chloropyrimidines with Tosylhydrazine;389
1.10.3.4.1.4.2;16.12.4.1.4.2 Halogen–Metal Exchange Reactions;389
1.10.3.4.1.4.2.1;16.12.4.1.4.2.1 Method 1: Formation of Stannylpyrimidines;389
1.10.3.4.1.4.2.2;16.12.4.1.4.2.2 Method 2: Formation of Pyrimidinylboronic Acids;391
1.10.3.4.1.4.2.3;16.12.4.1.4.2.3 Method 3: Formation of Pyrimidinylzinc Halides;391
1.10.3.4.1.4.2.4;16.12.4.1.4.2.4 Method 4: Formation of Pyrimidinylmagnesium Halides;393
1.10.3.4.1.4.3;16.12.4.1.4.3 Substitution of Halogens by Carbofunctional Groups;393
1.10.3.4.1.4.3.1;16.12.4.1.4.3.1 Method 1: Reaction with Carbonyl Compounds via Lithiated Intermediates;394
1.10.3.4.1.4.3.2;16.12.4.1.4.3.2 Method 2: Palladium-Catalyzed Cross Coupling with Alkenes or Alkynes (Heck-Type Reactions);396
1.10.3.4.1.4.3.2.1;16.12.4.1.4.3.2.1 Variation 1: Coupling with Alkenes;396
1.10.3.4.1.4.3.2.2;16.12.4.1.4.3.2.2 Variation 2: Coupling with Alkynes (Sonogashira Coupling);399
1.10.3.4.1.4.3.3;16.12.4.1.4.3.3 Method 3: Palladium-Catalyzed Cross Coupling with Organostannanes (Stille Reaction);404
1.10.3.4.1.4.3.4;16.12.4.1.4.3.4 Method 4: Palladium-Catalyzed Cross Coupling with Organozinc Reagents (Negishi Coupling);406
1.10.3.4.1.4.3.5;16.12.4.1.4.3.5 Method 5: Reaction with Arylboronic Acids (Suzuki and Suzuki–Miyaura Coupling);409
1.10.3.4.1.4.3.6;16.12.4.1.4.3.6 Method 6: Reaction with Aryl- or Alkyltrifluoroborates;414
1.10.3.4.1.4.3.7;16.12.4.1.4.3.7 Method 7: Reaction with Triaryl- or Trialkynylindiums;416
1.10.3.4.1.4.3.8;16.12.4.1.4.3.8 Method 8: Reaction with Grignard Reagents (Kumada Cross Coupling);417
1.10.3.4.1.4.3.9;16.12.4.1.4.3.9 Method 9: Reaction with Active Methylene Compounds;419
1.10.3.4.1.4.3.10;16.12.4.1.4.3.10 Method 10: Cyanation;421
1.10.3.4.1.4.3.11;16.12.4.1.4.3.11 Method 11: Other Substitution Reactions;423
1.10.3.4.1.4.4;16.12.4.1.4.4 Halogen-Exchange Reactions;425
1.10.3.4.1.4.4.1;16.12.4.1.4.4.1 Method 1: Exchange of Chlorine for Fluorine;425
1.10.3.4.1.4.4.2;16.12.4.1.4.4.2 Method 2: Exchange of Chlorine for Iodine;427
1.10.3.4.1.4.5;16.12.4.1.4.5 Substitution of Halogen by Oxygen Functions;429
1.10.3.4.1.4.5.1;16.12.4.1.4.5.1 Method 1: Hydrolysis of Halopyrimidines;429
1.10.3.4.1.4.5.2;16.12.4.1.4.5.2 Method 2: Exchange of Halogen for Alkoxides;430
1.10.3.4.1.4.6;16.12.4.1.4.6 Substitution of Halogen by Sulfur Functionalities;434
1.10.3.4.1.4.6.1;16.12.4.1.4.6.1 Method 1: Conversion of Halopyrimidines into Thiols;434
1.10.3.4.1.4.6.2;16.12.4.1.4.6.2 Method 2: Reaction of Halopyrimidines with Thiolates;436
1.10.3.4.1.4.7;16.12.4.1.4.7 Substitution of Halogens by Nitrogen Functionalities;439
1.10.3.4.1.4.7.1;16.12.4.1.4.7.1 Method 1: Substitution of Halogens by Ammonia;439
1.10.3.4.1.4.7.2;16.12.4.1.4.7.2 Method 2: Substitution of Halogens by Aliphatic Amines;441
1.10.3.4.1.4.7.3;16.12.4.1.4.7.3 Method 3: Substitution of Halogens by Aromatic Amines;445
1.10.3.4.1.4.7.4;16.12.4.1.4.7.4 Method 4: Substitution of Halogens by N-Heterocycles;449
1.10.3.4.1.4.7.5;16.12.4.1.4.7.5 Method 5: Substitution of Halogens by Sulfonamides;449
1.10.3.4.1.4.7.6;16.12.4.1.4.7.6 Method 6: Substitution of Halogens by Hydrazines;450
1.10.3.4.1.4.7.7;16.12.4.1.4.7.7 Method 7: Substitution of Halogens by Azide;451
1.10.3.4.1.4.8;16.12.4.1.4.8 Substitution of Oxygen Functions;452
1.10.3.4.1.4.8.1;16.12.4.1.4.8.1 Method 1: Exchange of Oxygen for a Carbofunctional Group;452
1.10.3.4.1.4.8.2;16.12.4.1.4.8.2 Method 2: Exchange of Hydroxy for Halogen;453
1.10.3.4.1.4.8.2.1;16.12.4.1.4.8.2.1 Variation 1: Introduction of Chlorine;453
1.10.3.4.1.4.8.2.2;16.12.4.1.4.8.2.2 Variation 2: Introduction of Bromine;456
1.10.3.4.1.4.8.3;16.12.4.1.4.8.3 Method 3: Exchange of Hydroxy for Alkoxy and Aryloxy;458
1.10.3.4.1.4.8.4;16.12.4.1.4.8.4 Method 4: Exchange of Oxygen for Sulfur;459
1.10.3.4.1.4.8.5;16.12.4.1.4.8.5 Method 5: Exchange of Hydroxy for Amino;460
1.10.3.4.1.4.9;16.12.4.1.4.9 Substitution of Sulfur Functions;462
1.10.3.4.1.4.9.1;16.12.4.1.4.9.1 Method 1: Desulfurization;463
1.10.3.4.1.4.9.1.1;16.12.4.1.4.9.1.1 Variation 1: Reduction with Raney Nickel;463
1.10.3.4.1.4.9.1.2;16.12.4.1.4.9.1.2 Variation 2: Detosylation;463
1.10.3.4.1.4.9.2;16.12.4.1.4.9.2 Method 2: Exchange for Carbofunctional Groups;464
1.10.3.4.1.4.9.3;16.12.4.1.4.9.3 Method 3: Exchange for Hydroxy and Alkoxy Groups;466
1.10.3.4.1.4.9.4;16.12.4.1.4.9.4 Method 4: Exchange for Amino Groups;468
1.10.3.4.1.4.10;16.12.4.1.4.10 Substitution of Amino Groups;470
1.10.3.4.1.4.10.1;16.12.4.1.4.10.1 Method 1: Conversion of Pyrimidin-2-amines into 2-Phenylpyrimidines;471
1.10.3.4.1.5;16.12.4.1.5 Solid-Phase Synthesis Based on Substitution Reactions;471
1.10.3.4.2;16.12.4.2 Addition Reactions;478
1.10.3.4.2.1;16.12.4.2.1 Addition of Organic Groups;478
1.10.3.4.2.1.1;16.12.4.2.1.1 Method 1: N-Alkylations;478
1.10.3.4.2.1.2;16.12.4.2.1.2 Method 2: C-Alkylations;479
1.10.3.4.2.2;16.12.4.2.2 Addition of Heteroatoms;480
1.10.3.4.2.2.1;16.12.4.2.2.1 Method 1: Generation of N-Oxides;480
1.10.3.4.3;16.12.4.3 Rearrangement of Substituents;483
1.10.3.4.3.1;16.12.4.3.1 Method 1: Dimroth Rearrangement;483
1.10.3.4.3.2;16.12.4.3.2 Method 2: Conversion of 3-Phenyl-2H-isoxazolo[2,3-a]pyrimidin-2-ones into 2-Benzoylpyrimidines;484
1.10.3.4.3.3;16.12.4.3.3 Method 3: Conversion of 3H-[1,2,4]Thiadiazolo[4,3-c]pyrimidin-3-ones into Pyrimidin-4-ylcarbamates;485
1.10.3.4.4;16.12.4.4 Modification of Substituents;486
1.10.3.4.4.1;16.12.4.4.1 Modification of Carbon Functions;486
1.10.3.4.4.1.1;16.12.4.4.1.1 Method 1: Modification of 5-(Ethoxymethyl)pyrimidines;486
1.10.3.4.4.1.2;16.12.4.4.1.2 Method 2: Conversion of Methyl into Pyrazol-4-yl;487
1.10.3.4.4.1.3;16.12.4.4.1.3 Method 3: Conversion of Ethynyl into Indol-3-yl;488
1.10.3.4.4.2;16.12.4.4.2 Modification of Oxygen Functions;488
1.10.3.4.4.2.1;16.12.4.4.2.1 Method 1: O-Alkylation and O-Arylation;488
1.10.3.4.4.2.2;16.12.4.4.2.2 Method 2: O-Acylation;490
1.10.3.4.4.2.3;16.12.4.4.2.3 Method 3: O-Silylation;492
1.10.3.4.4.2.4;16.12.4.4.2.4 Method 4: O-Sulfonation;492
1.10.3.4.4.3;16.12.4.4.3 Modification of Sulfur Functions;493
1.10.3.4.4.3.1;16.12.4.4.3.1 Method 1: S-Alkylation and S-Dealkylation;493
1.10.3.4.4.3.2;16.12.4.4.3.2 Method 2: S-Oxidation;494
1.10.3.4.4.4;16.12.4.4.4 Modification of Nitrogen Functions;496
1.10.3.4.4.4.1;16.12.4.4.4.1 Method 1: Reduction of Nitro and Nitroso Groups;496
1.10.3.4.4.4.2;16.12.4.4.4.2 Method 2: Arylation of Primary Amino Groups;497
1.11;Volume 39: Sulfur, Selenium, and Tellurium;526
1.11.1;39.17 Product Class 17: Acyclic Dialkyl Selenoxides and Derivatives;526
1.11.1.1;39.17.3 Acyclic Dialkyl Selenoxides and Derivatives;526
1.11.1.1.1;39.17.3.1 Applications of Acyclic Dialkylselenium Dihalides in Organic Synthesis;526
1.11.1.1.1.1;39.17.3.1.1 Utilization of Dialkylselenium Dihalides as Reagents;526
1.11.1.1.1.1.1;39.17.3.1.1.1 Method 1: Reduction of Tertiary Amides;526
1.11.1.1.1.1.2;39.17.3.1.1.2 Method 2: Reduction of Nitriles;527
1.11.1.1.1.1.3;39.17.3.1.1.3 Method 3: Transformation of Alcohols into the Corresponding Halides;528
1.11.1.1.1.1.4;39.17.3.1.1.4 Method 4: Transformation of Alcohols into Alkyl Chlorides;529
1.11.1.1.1.1.5;39.17.3.1.1.5 Method 5: Selenation of Metallocene-1,1'-dichalcogenols;530
1.11.1.1.1.2;39.17.3.1.2 Transformation of Dialkylselenium Dihalides;531
1.11.1.1.1.2.1;39.17.3.1.2.1 Method 1: Transformation into Dialkylselenium Diazides;531
1.11.1.1.1.2.2;39.17.3.1.2.2 Method 2: Dehalogenation into Selenides;531
1.11.1.1.1.2.3;39.17.3.1.2.3 Method 3: Migration of Chlorine;533
1.11.1.1.1.2.4;39.17.3.1.2.4 Method 4: Addition with Ring Opening of Tetrahydrofuran;534
1.12;Author Index;536
1.13;Abbreviations;570
1.14;List of All Volumes;576
