E-Book, Englisch, 520 Seiten, PDF
Reihe: Science of Synthesis
E-Book, Englisch, 520 Seiten, PDF
Reihe: Science of Synthesis
ISBN: 978-3-13-242318-3
Verlag: Thieme
Format: PDF
Kopierschutz: Adobe DRM (»Systemvoraussetzungen)
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- Medizin | Veterinärmedizin Medizin | Public Health | Pharmazie | Zahnmedizin Medizinische Fachgebiete Bildgebende Verfahren, Nuklearmedizin, Strahlentherapie Magnetresonanztomographie, Computertomographie (MRT, CT)
- Medizin | Veterinärmedizin Medizin | Public Health | Pharmazie | Zahnmedizin Medizinische Fachgebiete Bildgebende Verfahren, Nuklearmedizin, Strahlentherapie Radiologie, Bildgebende Verfahren
- Medizin | Veterinärmedizin Medizin | Public Health | Pharmazie | Zahnmedizin Chirurgie Orthopädie- und Unfallchirurgie
Weitere Infos & Material
1;Science of Synthesis: Knowledge Updates 2018/2;1
2;Title Page;7
3;Copyright;8
4;Preface;9
5;Abstracts;11
6;Overview;13
7;Table of Contents;15
8;10.23 Product Class 23: Pyrido[X,Y-b]indoles (Carbolines);33
8.1;10.23.1 Product Subclass 1: 9H-Pyrido[2,3-b]indoles (?-Carbolines);38
8.1.1;10.23.1.1 Synthesis by Ring-Closure Reactions;38
8.1.1.1;10.23.1.1.1 By Annulation to an Arene;38
8.1.1.1.1;10.23.1.1.1.1 By Formation of Four N–C and Two C–C Bonds;38
8.1.1.1.1.1;10.23.1.1.1.1.1 With Formation of 1–2, 2–3, 4–4a, 1–9a, 8a–9, and 9–9a Bonds;38
8.1.1.1.1.1.1;10.23.1.1.1.1.1.1 Method 1: From 1-Bromo-2-(2,2-dibromovinyl)benzenes, Ammonia, and Alkyl Aldehydes;38
8.1.1.1.2;10.23.1.1.1.2 By Formation of Two N–C and One C–C Bonds;40
8.1.1.1.2.1;10.23.1.1.1.2.1 With Formation of 1–9a, 4–4a, and 9–9a Bonds;40
8.1.1.1.2.1.1;10.23.1.1.1.2.1.1 Method 1: From (2-Nitroaryl)acetonitriles and 3-Acetoxy-3-aryl-2-methylene Ketones;40
8.1.1.1.2.1.2;10.23.1.1.1.2.1.2 Method 2: From (2-Nitrophenyl)acetonitrile and 3-Arylenones;42
8.1.1.1.2.1.2.1;10.23.1.1.1.2.1.2.1 Variation 1: From (2-Nitrophenyl)acetonitrile and 4H-1-Benzopyran-4-ones;44
8.1.1.1.3;10.23.1.1.1.3 By Formation of Two N–C Bonds;45
8.1.1.1.3.1;10.23.1.1.1.3.1 With Formation of 8a–9 and 9–9a Bonds;45
8.1.1.1.3.1.1;10.23.1.1.1.3.1.1 Method 1: From Primary Amines and 3-(2-Bromophenyl)-2-chloropyridine;45
8.1.1.1.4;10.23.1.1.1.4 By Formation of One N–C Bond and One C–C Bond;47
8.1.1.1.4.1;10.23.1.1.1.4.1 With Formation of 4a–4b and 9–9a Bonds;47
8.1.1.1.4.1.1;10.23.1.1.1.4.1.1 Method 1: From 2,3-Dihalopyridines and Anilines;47
8.1.1.1.4.1.2;10.23.1.1.1.4.1.2 Method 2: From 2-Iodopyridine and a 2-Bromoaniline;48
8.1.1.1.5;10.23.1.1.1.5 By Formation of Two C–C Bonds;49
8.1.1.1.5.1;10.23.1.1.1.5.1 With Formation of 3–4 and 4a–9a Bonds;49
8.1.1.1.5.1.1;10.23.1.1.1.5.1.1 Method 1: From (2-Alkenylaryl)carbodiimides;49
8.1.1.1.5.1.2;10.23.1.1.1.5.1.2 Method 2: From N-Acyl-N-(2-alkynylaryl)pyrimidin-2-amines or 3-[(2-Alkynylphenyl)amino]pyrazin-2-ones;51
8.1.1.1.6;10.23.1.1.1.6 By Formation of One N–C Bond;53
8.1.1.1.6.1;10.23.1.1.1.6.1 With Formation of the 9–9a Bond;53
8.1.1.1.6.1.1;10.23.1.1.1.6.1.1 Method 1: From 3-(2-Azidoaryl)pyridines;53
8.1.1.1.6.1.1.1;10.23.1.1.1.6.1.1.1 Variation 1: From 3-(2-Azidoaryl)pyridinium Trifluoromethanesulfonates and a Rhodium Catalyst;54
8.1.1.1.6.1.2;10.23.1.1.1.6.1.2 Method 2: From 3-(2-Nitroaryl)pyridines;55
8.1.1.1.6.1.2.1;10.23.1.1.1.6.1.2.1 Variation 1: From 3-(2-Nitrosoaryl)pyridines;56
8.1.1.1.6.1.3;10.23.1.1.1.6.1.3 Method 3: From 2-(3-Pyridyl)-N-tosylanilines or N-Acetyl-2-(3-pyridyl)-anilines;56
8.1.1.1.6.1.4;10.23.1.1.1.6.1.4 Method 4: From N-[2-(2-Fluoropyridin-3-yl)phenyl]pivalamide;58
8.1.1.1.7;10.23.1.1.1.7 By Formation of One C–C Bond;58
8.1.1.1.7.1;10.23.1.1.1.7.1 With Formation of the 4a–4b Bond;58
8.1.1.1.7.1.1;10.23.1.1.1.7.1.1 Method 1: From N-Arylpyridin-2-amines;58
8.1.1.1.7.1.1.1;10.23.1.1.1.7.1.1.1 Variation 1: From N,N-Diphenylpyridin-2-amine or N-Methyl-N-phenylpyridin-2-amine;59
8.1.1.1.7.1.2;10.23.1.1.1.7.1.2 Method 2: From N2-Phenylpyridine-2,3-diamines;60
8.1.1.1.7.1.3;10.23.1.1.1.7.1.3 Method 3: From an N-Arylpyridin-2-amine with at Least One Halogen on at Least One Ring;61
8.1.1.1.7.1.3.1;10.23.1.1.1.7.1.3.1 Variation 1: From N-Aryl-3-chloropyridin-2-amines by Palladium Catalysis;61
8.1.1.1.7.1.3.2;10.23.1.1.1.7.1.3.2 Variation 2: From N-Aryl-3-bromopyridin-2-amines with Palladium Catalysis;62
8.1.1.1.7.1.3.3;10.23.1.1.1.7.1.3.3 Variation 3: From N-[3-Chloro-1-methylpyridin-2(1H)-ylidene]anilines;65
8.1.1.1.7.1.3.4;10.23.1.1.1.7.1.3.4 Variation 4: From N-(Chloroaryl)-3-chloro-1-methylpyridin-2(1H)-imines and Secondary Amines;66
8.1.1.1.7.1.3.5;10.23.1.1.1.7.1.3.5 Variation 5: From N-Aryl-3-halopyridin-2-amines by Photostimulated SRN1 Reactions;69
8.1.1.1.7.1.3.6;10.23.1.1.1.7.1.3.6 Variation 6: From 3-Bromo-N-(2-bromophenyl)pyridin-2-amines by Palladium(0)-Catalyzed Bond Formation via Tributylstannyl Intermediates;71
8.1.1.2;10.23.1.1.2 By Annulation to a Heterocycle;71
8.1.1.2.1;10.23.1.1.2.1 By Annulation to a Pyridine;71
8.1.1.2.1.1;10.23.1.1.2.1.1 By Formation of One N–C and One C–C Bond;71
8.1.1.2.1.1.1;10.23.1.1.2.1.1.1 With Formation of 4a–4b and 8a–9 Bonds;71
8.1.1.2.1.1.1.1;10.23.1.1.2.1.1.1.1 Method 1: From Pyridin-2,4,6-triamine;71
8.1.1.2.2;10.23.1.1.2.2 By Annulation to an Indole;72
8.1.1.2.2.1;10.23.1.1.2.2.1 By Formation of Two N–C and One C–C Bonds;72
8.1.1.2.2.1.1;10.23.1.1.2.2.1.1 With Formation of 1–2, 1–9a, and 4–4a Bonds;72
8.1.1.2.2.1.1.1;10.23.1.1.2.2.1.1.1 Method 1: From 2-Bromo-1H-indole;72
8.1.1.2.2.2;10.23.1.1.2.2.2 By Formation of One N–C and Two C–C Bonds;73
8.1.1.2.2.2.1;10.23.1.1.2.2.2.1 With Formation of 1–2, 2–3, and 4–4a Bonds;73
8.1.1.2.2.2.1.1;10.23.1.1.2.2.2.1.1 Method 1: From Ethyl 2-Amino-1H-indole-3-carboxylates, an Arylacetylene, and an Aryl Aldehyde;73
8.1.1.2.2.3;10.23.1.1.2.2.3 By Formation of Two N–C Bonds;75
8.1.1.2.2.3.1;10.23.1.1.2.2.3.1 With Formation of 1–2 and 1–9a Bonds;75
8.1.1.2.2.3.1.1;10.23.1.1.2.2.3.1.1 Method 1: From 1,5-Dicarbonyl Compounds or Equivalents;75
8.1.1.2.2.4;10.23.1.1.2.2.4 By Formation of One N–C and One C–C Bonds;78
8.1.1.2.2.4.1;10.23.1.1.2.2.4.1 With Formation of 1–2 and 4–4a Bonds;78
8.1.1.2.2.4.1.1;10.23.1.1.2.2.4.1.1 Method 1: From 1H-Indol-2-amines and Alkynones;78
8.1.1.2.2.4.1.1.1;10.23.1.1.2.2.4.1.1.1 Variation 1: From 1H-Indol-2-amines and 1,3-Diketones;80
8.1.1.2.2.4.1.1.2;10.23.1.1.2.2.4.1.1.2 Variation 2: From N-(Phosphoranylidene)indol-2-amines;81
8.1.1.2.2.4.1.2;10.23.1.1.2.2.4.1.2 Method 2: From N-(Arylsulfonyl)-3-diazo-1,3-dihydroindol-2-imines;82
8.1.1.2.2.4.2;10.23.1.1.2.2.4.2 With Formation of 1–2 and 2–3 Bonds;84
8.1.1.2.2.4.2.1;10.23.1.1.2.2.4.2.1 Method 1: From 3-Alkenyl-N-(triphenylphosphoranylidene)-1H-indol-2-amines;84
8.1.1.2.2.4.2.1.1;10.23.1.1.2.2.4.2.1.1 Variation 1: From 3-(2-Nitrovinyl)-N-(triphenylphosphoranylidene)-1H-indol-2-amines;85
8.1.1.2.2.4.3;10.23.1.1.2.2.4.3 With Formation of 1–2 and 3–4 Bonds;86
8.1.1.2.2.4.3.1;10.23.1.1.2.2.4.3.1 Method 1: From a 2-Amino-1H-indole-3-carbothioaldehyde;86
8.1.1.2.2.4.4;10.23.1.1.2.2.4.4 With Formation of 1–9a and 3–4 Bonds;87
8.1.1.2.2.4.4.1;10.23.1.1.2.2.4.4.1 Method 1: From 3-[Bis(methylsulfanyl)methylene]-1-methyl-1,3-dihydro-2H-indol-2-one;87
8.1.1.2.2.5;10.23.1.1.2.2.5 By Formation of Two C–C Bonds;88
8.1.1.2.2.5.1;10.23.1.1.2.2.5.1 With Formation of 3–4 and 4–4a Bonds;88
8.1.1.2.2.5.1.1;10.23.1.1.2.2.5.1.1 Method 1: From N-(1H-Indol-2-yl)acetamide;88
8.1.1.2.2.6;10.23.1.1.2.2.6 By Formation of One N–C Bond;88
8.1.1.2.2.6.1;10.23.1.1.2.2.6.1 With Formation of the 1–9b Bond;88
8.1.1.2.2.6.1.1;10.23.1.1.2.2.6.1.1 Method 1: From 3-(1H-Indol-3-yl)allyl Azides;88
8.1.1.2.2.6.1.2;10.23.1.1.2.2.6.1.2 Method 2: From 3-(1H-Indol-3-yl)propanone O-2,4-Dinitrophenyl Oximes;89
8.1.1.2.2.6.1.2.1;10.23.1.1.2.2.6.1.2.1 Variation 1: From 3-(1H-Indol-3-yl)propanone O-Pentafluorobenzoyl Oximes;90
8.1.1.2.2.6.1.2.2;10.23.1.1.2.2.6.1.2.2 Variation 2: From 3-(1H-Indol-3-yl)propanone O-Acetyl Oximes;91
8.1.1.2.2.6.1.2.3;10.23.1.1.2.2.6.1.2.3 Variation 3: From 3-(1H-Indol-3-yl)prop-2-enone O-Methyl Oximes;92
8.1.1.2.2.6.1.3;10.23.1.1.2.2.6.1.3 Method 3: From a 3-(2-Bromo-1H-indol-3-yl)allylamine;93
8.1.1.2.2.6.2;10.23.1.1.2.2.6.2 With Formation of the 1–2 Bond;94
8.1.1.2.2.6.2.1;10.23.1.1.2.2.6.2.1 Method 1: From a 3-Propargyl-1H-indol-2-amine;94
8.1.1.2.2.6.2.2;10.23.1.1.2.2.6.2.2 Method 2: From a 3-(2-Amino-1H-indol-3-yl)-2-cyanoacrylate;96
8.1.1.2.2.6.2.3;10.23.1.1.2.2.6.2.3 Method 3: From N'-[3-(2-Aroylvinyl)-1H-indol-2-yl]alkanimidamides;97
8.1.1.2.2.7;10.23.1.1.2.2.7 By Formation of One C–C Bond;98
8.1.1.2.2.7.1;10.23.1.1.2.2.7.1 With Formation of the 2–3 Bond;98
8.1.1.2.2.7.1.1;10.23.1.1.2.2.7.1.1 Method 1: From 3-Acetyl-2-(acylamino)-1H-indoles with Phosphoryl Chloride;98
8.1.1.2.2.7.1.1.1;10.23.1.1.2.2.7.1.1.1 Variation 1: From 3-Acetyl-2-(acylamino)-1H-indoles with Potassium tert-Butoxide;100
8.1.1.2.2.7.1.1.2;10.23.1.1.2.2.7.1.1.2 Variation 2: From N'-[3-(2-Aroylvinyl)-1H-indol-2-yl]alkanimidamides;101
8.1.1.2.2.7.2;10.23.1.1.2.2.7.2 With Formation of the 3–4 Bond;102
8.1.1.2.2.7.2.1;10.23.1.1.2.2.7.2.1 Method 1: From N'-(3-Cyano-1H-indol-2-yl)acetimidamides;102
8.1.1.2.2.7.2.2;10.23.1.1.2.2.7.2.2 Method 2: From N'-(3-Formyl-1H-indol-2-yl)alkanimidamides;103
8.1.1.2.2.7.2.3;10.23.1.1.2.2.7.2.3 Method 3: From a 2-Amino-1H-indole-3-carboxylate and a 1,3-Oxo Ester Equivalent;104
8.1.1.2.3;10.23.1.1.2.3 By Annulation to a 1H-Pyrrolo[2,3-b]pyridine (a 7-Azaindole);105
8.1.1.2.3.1;10.23.1.1.2.3.1 By Formation of Three C–C Bonds;105
8.1.1.2.3.1.1;10.23.1.1.2.3.1.1 With Formation of 4b–5, 6–7, and 8–8a Bonds;105
8.1.1.2.3.1.1.1;10.23.1.1.2.3.1.1.1 Method 1: From a 1H-Pyrrolo[2,3-b]pyridine and Two Equivalents of Methyl Acrylate;105
8.1.1.2.3.2;10.23.1.1.2.3.2 By Formation of Two C–C Bonds;106
8.1.1.2.3.2.1;10.23.1.1.2.3.2.1 With Formation of 4b–5 and 8–8a Bonds;106
8.1.1.2.3.2.1.1;10.23.1.1.2.3.2.1.1 Method 1: From a 1H-Pyrrolo[2,3-b]pyridine-3-boronic Acid;106
8.1.1.2.3.2.2;10.23.1.1.2.3.2.2 With Formation of 4b–5 and 6–7 Bonds;106
8.1.1.2.3.2.2.1;10.23.1.1.2.3.2.2.1 Method 1: From a 2-Vinyl-1H-pyrrolo[2,3-b]pyridine;106
8.1.1.2.3.2.3;10.23.1.1.2.3.2.3 With Formation of 6–7 and 8–8b Bonds;108
8.1.1.2.3.2.3.1;10.23.1.1.2.3.2.3.1 Method 1: From a 3-Vinyl-1H-pyrrolo[2,3-b]pyridine;108
8.1.1.2.3.3;10.23.1.1.2.3.3 By Formation of One C–C Bond;108
8.1.1.2.3.3.1;10.23.1.1.2.3.3.1 With Formation of the 8–8a Bond;108
8.1.1.2.3.3.1.1;10.23.1.1.2.3.3.1.1 Method 1: Intramolecular Acylation;108
8.1.2;10.23.1.2 Synthesis by Ring Transformation;109
8.1.2.1;10.23.1.2.1 Method 1: From 1-(2-Pyridyl)-1H-benzotriazoles;109
8.1.2.2;10.23.1.2.2 Method 2: From 3-Aryl-3H-[1,2,3]-triazolo[4,5-b]pyridines;110
8.1.3;10.23.1.3 Aromatization;111
8.1.4;10.23.1.4 Synthesis by Substituent Modification;114
8.1.4.1;10.23.1.4.1 Substitution of Existing Substituents;114
8.1.4.1.1;10.23.1.4.1.1 Substitution of N-Hydrogen;114
8.1.4.1.1.1;10.23.1.4.1.1.1 Giving N-Sulfur 9H-Pyrido[2,3-b]indoles;114
8.1.4.1.1.2;10.23.1.4.1.1.2 Giving N-Carbon 9H-Pyrido[2,3-b]indoles;115
8.1.4.1.1.2.1;10.23.1.4.1.1.2.1 Method 1: Using an Alkyl or Aryl Halide;115
8.1.4.1.1.2.2;10.23.1.4.1.1.2.2 Method 2: Via 1-Alkyl-9H-pyrido[2,3-b]indol-1-ium Salts;118
8.1.4.1.1.2.3;10.23.1.4.1.1.2.3 Method 3: Using Acyl Halides or Anhydrides;119
8.1.4.1.2;10.23.1.4.1.2 Substitution of N-Carbon and N-Sulfur;120
8.1.4.1.2.1;10.23.1.4.1.2.1 Giving N-Hydrogen 9H-Pyrido[2,3-b]indoles;120
8.1.4.1.2.1.1;10.23.1.4.1.2.1.1 Method 1: N-Deprotection;120
8.1.4.1.3;10.23.1.4.1.3 Substitution of C-Hydrogen;121
8.1.4.1.3.1;10.23.1.4.1.3.1 Direct Substitution by Electrophiles;121
8.1.4.1.3.1.1;10.23.1.4.1.3.1.1 Method 1: Giving C-Halogen 9H-Pyrido[2,3-b]indoles;121
8.1.4.1.3.1.2;10.23.1.4.1.3.1.2 Method 2: Giving C-Sulfur 9H-Pyrido[2,3-b]indoles;122
8.1.4.1.3.1.3;10.23.1.4.1.3.1.3 Method 3: Giving C-Nitrogen 9H-Pyrido[2,3-b]indoles;123
8.1.4.1.3.1.4;10.23.1.4.1.3.1.4 Method 4: Giving C-Carbon 9H-Pyrido[2,3-b]indoles;124
8.1.4.1.3.2;10.23.1.4.1.3.2 Substitution via Metalation;124
8.1.4.1.3.3;10.23.1.4.1.3.3 Substitution via 1-Oxides;126
8.1.4.1.3.4;10.23.1.4.1.3.4 Substitution via Displacement of Halogen;130
8.1.4.1.3.4.1;10.23.1.4.1.3.4.1 Method 1: Direct Nucleophilic Displacement;130
8.1.4.1.3.4.2;10.23.1.4.1.3.4.2 Method 2: Substitution of Halogen via Cross-Coupling Processes;133
8.1.4.1.3.4.2.1;10.23.1.4.1.3.4.2.1 Variation 1: Forming Amines;133
8.1.4.1.3.4.2.2;10.23.1.4.1.3.4.2.2 Variation 2: Forming Phenolic Ethers;135
8.1.4.1.3.4.2.3;10.23.1.4.1.3.4.2.3 Variation 3: Adding Carbon Substituents;136
8.1.4.2;10.23.1.4.2 Modification of Substituents;141
8.1.4.2.1;10.23.1.4.2.1 Modification of C-Oxygen Functionalities;141
8.1.4.2.1.1;10.23.1.4.2.1.1 Method 1: Giving C-Halogen;141
8.1.4.2.1.2;10.23.1.4.2.1.2 Method 2: Giving Quinones;141
8.1.4.2.1.3;10.23.1.4.2.1.3 Method 3: Giving Phenolic Ethers;142
8.1.4.2.2;10.23.1.4.2.2 Modification of C-Nitrogen Functionalities;142
8.1.4.2.2.1;10.23.1.4.2.2.1 Method 1: Giving C-Nitrogen 9H-Pyrido[2,3-b]indoles;142
8.1.4.2.2.2;10.23.1.4.2.2.2 Method 2: Giving C-Halogen 9H-Pyrido[2,3-b]indoles;143
8.1.4.2.2.3;10.23.1.4.2.2.3 Method 3: Giving C-Carbon 9H-Pyrido[2,3-b]indoles;143
8.1.4.2.3;10.23.1.4.2.3 Modification of C-Carbon Functionalities;144
8.1.4.2.3.1;10.23.1.4.2.3.1 Method 1: Giving C-Carbon 5H-Pyrido[3,2-b]indoles;144
8.2;10.23.2 Product Subclass 2: 9H-Pyrido[3,4-b]indoles (?-Carbolines);146
8.2.1;10.23.2.1 Synthesis by Ring-Closure Reactions;146
8.2.1.1;10.23.2.1.1 By Annulation to an Arene;146
8.2.1.1.1;10.23.2.1.1.1 By Formation of One N–C and Two C–C Bonds;146
8.2.1.1.1.1;10.23.2.1.1.1.1 With Formation of 1–2, 3–4, and 4a–9b Bonds;146
8.2.1.1.1.1.1;10.23.2.1.1.1.1.1 Method 1: From 2,N-Dialkynyl-N-tosylanilines and Methyl Cyanoformate;146
8.2.1.1.1.1.2;10.23.2.1.1.1.1.2 Method 2: By Intramolecular Reaction of a Cyano-Substituted 2,N-Dialkynyl-N-tosylaniline;147
8.2.1.1.2;10.23.2.1.1.2 By Formation of One N–C Bond and One C–C Bond;148
8.2.1.1.2.1;10.23.2.1.1.2.1 With Formation of 4a–4b and 9–9a Bonds;148
8.2.1.1.2.1.1;10.23.2.1.1.2.1.1 Method 1: From (2-Aminophenyl)boronic Acid;148
8.2.1.1.3;10.23.2.1.1.3 By Formation of Two C–C Bonds;149
8.2.1.1.3.1;10.23.2.1.1.3.1 With Formation of 3–4 and 4a–9a Bonds;149
8.2.1.1.3.1.1;10.23.2.1.1.3.1.1 Method 1: From 3-[(2-Alkynylphenyl)amino]pyrazin-2-ones;149
8.2.1.1.4;10.23.2.1.1.4 By Formation of One N–C Bond;150
8.2.1.1.4.1;10.23.2.1.1.4.1 With Formation of the 2–3 Bond;150
8.2.1.1.4.1.1;10.23.2.1.1.4.1.1 Method 1: From 3-Alkynyl-1H-indole-2-carbaldehyde Oximes;150
8.2.1.1.4.1.2;10.23.2.1.1.4.1.2 Method 2: From 3-Alkenyl-1H-indole-2-carbaldehyde Oximes;150
8.2.1.1.4.1.3;10.23.2.1.1.4.1.3 Method 3: From 3-Alkynyl-1H-indole-2-carboxamides;151
8.2.1.1.4.2;10.23.2.1.1.4.2 With Formation of the 8a–9 Bond;152
8.2.1.1.4.2.1;10.23.2.1.1.4.2.1 Method 1: From 4-Aryl-3-nitropyridines;152
8.2.1.1.4.2.2;10.23.2.1.1.4.2.2 Method 2: From 4-(2-Bromoaryl)pyridin-3-amines;153
8.2.1.1.4.2.3;10.23.2.1.1.4.2.3 Method 3: From 3-Acetamido-4-(2-bromoaryl)-3,4-dihydropyridin-2-ones;154
8.2.1.1.4.3;10.23.2.1.1.4.3 With Formation of the 9–9a Bond;154
8.2.1.1.4.3.1;10.23.2.1.1.4.3.1 Method 1: From a 4-(2-Azidophenyl)pyridine by Thermolysis;154
8.2.1.1.4.3.2;10.23.2.1.1.4.3.2 Method 2: From 4-(2-Azidoaryl)pyridinium Trifluoromethanesulfonates and a Rhodium Catalyst;155
8.2.1.1.4.3.3;10.23.2.1.1.4.3.3 Method 3: From 4-(2-Nitroaryl)pyridines;157
8.2.1.1.4.3.4;10.23.2.1.1.4.3.4 Method 4: From 2-(3-Halopyridin-4-yl)anilines;157
8.2.1.1.4.3.5;10.23.2.1.1.4.3.5 Method 5: From N-[2-(3-Fluoropyridin-4-yl)phenyl]pivalamides;158
8.2.1.1.4.3.6;10.23.2.1.1.4.3.6 Method 6: From 2-(2-Chloropyridin-4-yl)-N-tosylanilines;159
8.2.1.1.5;10.23.2.1.1.5 By Formation of One C–C Bond;160
8.2.1.1.5.1;10.23.2.1.1.5.1 With Formation of the 4a–4b Bond;160
8.2.1.1.5.1.1;10.23.2.1.1.5.1.1 Method 1: From an N-Arylpyridin-3-amine by Irradiation;160
8.2.1.1.5.1.2;10.23.2.1.1.5.1.2 Method 2: From N-(2-Haloaryl)pyridin-3-amines by Palladium(0)-Catalyzed Bond Formation;161
8.2.1.1.5.1.3;10.23.2.1.1.5.1.3 Method 3: From 4-Halo-N-phenylpyridin-3-amines by Intramolecular Palladium(0)-Catalyzed Bond Formation;163
8.2.1.1.5.1.4;10.23.2.1.1.5.1.4 Method 4: From 4-Bromo-N-phenylpyridin-3-amines by Intramolecular Photostimulated SRN1 Reaction;163
8.2.1.1.5.1.5;10.23.2.1.1.5.1.5 Method 5: From 4-Bromo-N-(2-bromophenyl)pyridin-3-amines by Palladium(0)-Catalyzed Bond Formation via Tributylstannyl Intermediates;164
8.2.1.1.5.1.6;10.23.2.1.1.5.1.6 Method 6: From an N-(2-Diazophenyl)-N-methylpyridin-3-amine;165
8.2.1.2;10.23.2.1.2 By Annulation to a Heterocycle;165
8.2.1.2.1;10.23.2.1.2.1 By Annulation to an Indole;165
8.2.1.2.1.1;10.23.2.1.2.1.1 By Formation of Two N–C Bonds;166
8.2.1.2.1.1.1;10.23.2.1.2.1.1.1 With Formation of 1–2 and 2–3 Bonds;166
8.2.1.2.1.1.1.1;10.23.2.1.2.1.1.1.1 Method 1: From 1H-Indolic 1,5-Dicarbonyls and Ammonia;166
8.2.1.2.1.1.1.1.1;10.23.2.1.2.1.1.1.1.1 Variation 1: From 2-Acyl-3-(2-ethoxyvinyl)-1H-indoles and Ammonia;167
8.2.1.2.1.1.1.1.2;10.23.2.1.2.1.1.1.1.2 Variation 2: From Ethyl 3-[1-(Dimethylamino)-3-ethoxy-3-oxoprop-1-en-2-yl]-1-methyl-1H-indole-2-carboxylate;168
8.2.1.2.1.1.1.1.3;10.23.2.1.2.1.1.1.1.3 Variation 3: From 3-Alkynyl-1H-indole-2-carbaldehydes and Ammonia;168
8.2.1.2.1.1.1.1.4;10.23.2.1.2.1.1.1.1.4 Variation 4: From 2-Acyl-3-alkynyl-1H-indoles and Ammonia;169
8.2.1.2.1.2;10.23.2.1.2.1.2 By Formation of One N–C Bond and One C–C Bond;170
8.2.1.2.1.2.1;10.23.2.1.2.1.2.1 With Formation of 1–2 and 3–4 Bonds;170
8.2.1.2.1.2.1.1;10.23.2.1.2.1.2.1.1 Method 1: From Ethyl 3-(2-Ethoxy-2-oxoethyl)-1H-indole-2-carboxylate.;170
8.2.1.2.1.2.2;10.23.2.1.2.1.2.2 With Formation of 2–3 and 4–4a Bonds;171
8.2.1.2.1.2.2.1;10.23.2.1.2.1.2.2.1 Method 1: From tert-Butylimines of 1H-Indole-2-carbaldehydes;171
8.2.1.2.1.2.2.1.1;10.23.2.1.2.1.2.2.1.1 Variation 1: From tert-Butylimines of 3-Iodo-1H-indole-2-carbaldehydes;171
8.2.1.2.1.2.2.1.2;10.23.2.1.2.1.2.2.1.2 Variation 2: From tert-Butylimines of 3-Unsubstituted 1H-Indole-2-carbaldehydes;172
8.2.1.2.1.2.2.1.3;10.23.2.1.2.1.2.2.1.3 Variation 3: From O-Acetyloximes of 2-Acyl-1H-indoles and Internal Alkynes by a Copper/Rhodium Bimetallic Relay Catalyst;173
8.2.1.2.1.2.2.1.4;10.23.2.1.2.1.2.2.1.4 Variation 4: From a 2-(1-Azidovinyl)-1H-indole with an Internal Alkyne and Copper/Rhodium Bimetallic Catalysis;174
8.2.1.2.1.2.2.2;10.23.2.1.2.1.2.2.2 Method 2: From 1H-Indole-2-carboxamides;175
8.2.1.2.1.2.2.2.1;10.23.2.1.2.1.2.2.2.1 Variation 1: From 1-Alkyl-1H-indole-2-carboxamides with Internal Alkynes and Palladium(II) Acetate;175
8.2.1.2.1.2.2.2.2;10.23.2.1.2.1.2.2.2.2 Variation 2: From 1-Methyl-1H-indole-2-carboxamide with Diphenylacetylene and a Ruthenium Catalyst;176
8.2.1.2.1.2.2.2.3;10.23.2.1.2.1.2.2.2.3 Variation 3: From 1-Alkyl-1H-indole-2-carboxamides with Ethynyl N-Methyliminodiacetic Acid (MIDA) Boronate and a Rhodium Catalyst;176
8.2.1.2.1.2.2.2.4;10.23.2.1.2.1.2.2.2.4 Variation 4: From 1-Methyl-1H-indole-2-carboxamide with Vinyl Acetate;177
8.2.1.2.1.2.2.3;10.23.2.1.2.1.2.2.3 Method 3: From 2-(Azidomethyl)-1H-indoles and Ynamides;177
8.2.1.2.1.2.3;10.23.2.1.2.1.2.3 With Formation of 1–2 and 1–9a Bonds;179
8.2.1.2.1.2.3.1;10.23.2.1.2.1.2.3.1 Method 1: From 2-(1H-Indol-3-yl)ethan-1-amines (Tryptamines) and Aldehydes;179
8.2.1.2.1.2.3.1.1;10.23.2.1.2.1.2.3.1.1 Variation 1: With Hetaryl Aldehydes;179
8.2.1.2.1.2.3.1.2;10.23.2.1.2.1.2.3.1.2 Variation 2: With a-Oxoaldehydes;184
8.2.1.2.1.2.3.1.3;10.23.2.1.2.1.2.3.1.3 Variation 3: From Tryptamine with an Arylglyoxal and Palladium on Carbon;188
8.2.1.2.1.2.3.1.4;10.23.2.1.2.1.2.3.1.4 Variation 4: With Aryl Methyl Ketones or Styrenes;189
8.2.1.2.1.2.3.2;10.23.2.1.2.1.2.3.2 Method 2: From Tryptophan Esters or Amides and Trifluoroacetic Acid;190
8.2.1.2.1.2.3.3;10.23.2.1.2.1.2.3.3 Method 3: From Iminophosphoranes;191
8.2.1.2.1.2.4;10.23.2.1.2.1.2.4 With Formation of 2–3 and 1–9a Bonds;194
8.2.1.2.1.2.4.1;10.23.2.1.2.1.2.4.1 Method 1: From 3-Alkenyl-1H-indoles and an Oxime;194
8.2.1.2.1.3;10.23.2.1.2.1.3 By Formation of Two C–C Bonds;196
8.2.1.2.1.3.1;10.23.2.1.2.1.3.1 With Formation of 1–9a and 4–4a Bonds;196
8.2.1.2.1.3.1.1;10.23.2.1.2.1.3.1.1 Method 1: From a 1H-Indole and a 2-Aza-1,3-diene;196
8.2.1.2.1.3.1.2;10.23.2.1.2.1.3.1.2 Method 2: From 1H-Indoles and 1,2,4-Triazines via Cycloaddition then Elimination of Nitrogen;198
8.2.1.2.1.3.1.2.1;10.23.2.1.2.1.3.1.2.1 Variation 1: Intramolecularly from a 1-Acyl-1H-indole with a 1,2,4-Triazine Substituent;198
8.2.1.2.1.3.1.2.2;10.23.2.1.2.1.3.1.2.2 Variation 2: Intramolecularly from a 1-Alkyl-1H-indole with a 1,2,4-Triazine Substituent;198
8.2.1.2.1.3.1.2.3;10.23.2.1.2.1.3.1.2.3 Variation 3: Intermolecularly from 1H-Indoles and 1,2,4-Triazines;199
8.2.1.2.1.3.1.2.4;10.23.2.1.2.1.3.1.2.4 Variation 4: From 1H-Indoles and 1,2,4-Triazines Generated In Situ;200
8.2.1.2.1.4;10.23.2.1.2.1.4 By Formation of One N–C Bond;201
8.2.1.2.1.4.1;10.23.2.1.2.1.4.1 With Formation of the 1–2 Bond;201
8.2.1.2.1.4.1.1;10.23.2.1.2.1.4.1.1 Method 1: From a 2-[Bis(acetylsulfanyl)methyl]-1H-indole-3-pyruvate Oxime;201
8.2.1.2.1.4.1.2;10.23.2.1.2.1.4.1.2 Method 2: From a 2-{2-[Bis(methylsulfanyl)methylene]-2,3-dihydroindol-3-yl}acetonitrile;202
8.2.1.2.1.4.2;10.23.2.1.2.1.4.2 With Formation of the 2–3 Bond;202
8.2.1.2.1.4.2.1;10.23.2.1.2.1.4.2.1 Method 1: From 2-Acyl-3-alkenyl-1H-indole Oximes;202
8.2.1.2.1.4.2.2;10.23.2.1.2.1.4.2.2 Method 2: From 2-Acyl-3-alkynyl-1H-indole Imines or Oximes;204
8.2.1.2.1.4.2.3;10.23.2.1.2.1.4.2.3 Method 3: From tert-Butylimines of 3-Alkynyl-1H-indole-2-carbaldehydes;206
8.2.1.2.1.4.2.4;10.23.2.1.2.1.4.2.4 Method 4: From 3-Alkynyl-2-(azidomethyl)-1H-indoles;207
8.2.1.2.1.5;10.23.2.1.2.1.5 By Formation of One C–C Bond;207
8.2.1.2.1.5.1;10.23.2.1.2.1.5.1 With Formation of the 1–9a Bond;207
8.2.1.2.1.5.1.1;10.23.2.1.2.1.5.1.1 Method 1: From N-Acyltryptamines;207
8.2.1.2.1.5.2;10.23.2.1.2.1.5.2 With Formation of the 4–4a Bond;210
8.2.1.2.1.5.2.1;10.23.2.1.2.1.5.2.1 Method 1: From N-(2,2-Dialkoxyethyl)-1H-indole-2-carboxamides;210
8.2.1.2.1.5.2.2;10.23.2.1.2.1.5.2.2 Method 2: From an N-Allyl-3-iodo-1H-indole-2-carboxamide;212
8.2.1.2.1.5.2.3;10.23.2.1.2.1.5.2.3 Method 3: From an N-(2-Oxoalkyl)-1H-indole-2-carboxamide;212
8.2.1.2.1.5.2.4;10.23.2.1.2.1.5.2.4 Method 4: From an N-Propargyl-1H-indole-2-carboxamide;215
8.2.2;10.23.2.2 Synthesis by Ring Transformation;215
8.2.2.1;10.23.2.2.1 Method 1: From 1-(3-Pyridyl)-1H-benzotriazoles;215
8.2.2.2;10.23.2.2.2 Method 2: From 3-Aryl-3H-1,2,3-triazolo[4,5-c]pyridines;216
8.2.2.3;10.23.2.2.3 Method 3: From 4-[(1H-Indol-3-yl)methyl]oxazol-5(4H)-ones;216
8.2.2.4;10.23.2.2.4 Method 4: From Pyrano[3,4-b]indol-3(9H)-ones;217
8.2.3;10.23.2.3 Aromatization;218
8.2.3.1;10.23.2.3.1 Method 1: From 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indoles;219
8.2.3.2;10.23.2.3.2 Method 2: From 4,9-Dihydro-3H-pyrido[3,4-b]indoles;228
8.2.3.3;10.23.2.3.3 Method 3: From 2-Aryl-4,9-dihydro-3H-pyrido[3,4-b]indol-2-iums;233
8.2.3.4;10.23.2.3.4 Method 4: From 2,9-Dihydro-1H-pyrido[3,4-b]indoles;233
8.2.3.5;10.23.2.3.5 Method 5: From 6,7,8,9-Tetrahydro-5H-pyrido[3,4-b]indoles;237
8.2.4;10.23.2.4 Synthesis by Substituent Modification;238
8.2.4.1;10.23.2.4.1 Substitution of Existing Substituents;238
8.2.4.1.1;10.23.2.4.1.1 Substitution of N-Hydrogen;238
8.2.4.1.1.1;10.23.2.4.1.1.1 Giving N-Carbon 9H-Pyrido[3,4-b]indoles;238
8.2.4.1.1.1.1;10.23.2.4.1.1.1.1 Method 1: 9-Alkylation Using an Alkyl Halide;238
8.2.4.1.1.1.2;10.23.2.4.1.1.1.2 Method 2: 9-Arylation Using an Aryl Halide;240
8.2.4.1.1.1.3;10.23.2.4.1.1.1.3 Method 3: 9-Acylation;242
8.2.4.1.1.1.4;10.23.2.4.1.1.1.4 Method 4: 2-Alkylation Giving 2-Alkyl-9H-pyrido[3,4-b]indol-2-ium Salts and thence 2-Alkyl-2H-pyrido[3,4-b]indoles;243
8.2.4.1.2;10.23.2.4.1.2 Substitution of N-Carbon and N-Sulfur;247
8.2.4.1.2.1;10.23.2.4.1.2.1 Giving N-Hydrogen 9H-Pyrido[3,4-b]indoles;247
8.2.4.1.2.1.1;10.23.2.4.1.2.1.1 Method 1: N-Deprotection;247
8.2.4.1.3;10.23.2.4.1.3 Substitution of C-Hydrogen;248
8.2.4.1.3.1;10.23.2.4.1.3.1 Direct Substitution by Electrophiles;248
8.2.4.1.3.1.1;10.23.2.4.1.3.1.1 Method 1: Giving C-Halogen 9H-Pyrido[3,4-b]indoles;248
8.2.4.1.3.1.2;10.23.2.4.1.3.1.2 Method 2: Giving C-Sulfur 9H-Pyrido[3,4-b]indoles;250
8.2.4.1.3.1.3;10.23.2.4.1.3.1.3 Method 3: Giving C-Nitrogen 9H-Pyrido[3,4-b]indoles;251
8.2.4.1.3.1.4;10.23.2.4.1.3.1.4 Method 4: Giving C-Carbon 9H-Pyrido[3,4-b]indoles;252
8.2.4.1.3.2;10.23.2.4.1.3.2 Direct Substitution by Radicals;253
8.2.4.1.3.3;10.23.2.4.1.3.3 Substitution via Metalation;255
8.2.4.1.3.4;10.23.2.4.1.3.4 Substitution via 2-Oxides (N-Oxides);256
8.2.4.1.3.4.1;10.23.2.4.1.3.4.1 Variation 1: With Formation of 9H-Pyrido[3,4-b]indole-1-carbonitriles;257
8.2.4.1.3.4.2;10.23.2.4.1.3.4.2 Variation 2: With Formation of 9H-Pyrido[3,4-b]indol-1-ols (2,9-Dihydro-1H-pyrido[3,4-b]indol-1-ones);258
8.2.4.1.3.4.3;10.23.2.4.1.3.4.3 Variation 3: With Formation of 1-Halo-9H-pyrido[3,4-b]indoles;260
8.2.4.1.3.4.4;10.23.2.4.1.3.4.4 Variation 4: With Formation of 1-Carbon-9H-pyrido[3,4-b]indoles;260
8.2.4.1.3.5;10.23.2.4.1.3.5 Substitution via Displacement of Halogen;261
8.2.4.1.3.5.1;10.23.2.4.1.3.5.1 Method 1: Direct Nucleophilic Displacement;261
8.2.4.1.3.5.1.1;10.23.2.4.1.3.5.1.1 Variation 1: With Formation of Amines;261
8.2.4.1.3.5.1.2;10.23.2.4.1.3.5.1.2 Variation 2: With Formation of Ethers;262
8.2.4.1.3.5.1.3;10.23.2.4.1.3.5.1.3 Variation 3: With Formation of Halides;262
8.2.4.1.3.5.2;10.23.2.4.1.3.5.2 Method 2: Substitution of Halogen (or Trifluoromethanesulfonate) via Cross-Coupling Processes;263
8.2.4.1.3.5.2.1;10.23.2.4.1.3.5.2.1 Variation 1: Reaction at C1;263
8.2.4.1.3.5.2.2;10.23.2.4.1.3.5.2.2 Variation 2: Reaction at C4;266
8.2.4.1.3.5.2.3;10.23.2.4.1.3.5.2.3 Variation 3: Reaction at Benzene Ring Positions;267
8.2.4.1.3.6;10.23.2.4.1.3.6 Substitution via Displacement of Oxygen;268
8.2.4.2;10.23.2.4.2 Modification of Substituents;268
8.2.4.2.1;10.23.2.4.2.1 Modification of C-Oxygen Functionalities;268
8.2.4.2.1.1;10.23.2.4.2.1.1 Method 1: Giving C-Halogen;268
8.2.4.2.1.2;10.23.2.4.2.1.2 Method 2: Giving C-Oxygen;269
8.2.4.2.2;10.23.2.4.2.2 Modification of C-Nitrogen Functionalities;272
8.2.4.2.2.1;10.23.2.4.2.2.1 Method 1: Giving C-Nitrogen;272
8.2.4.2.2.2;10.23.2.4.2.2.2 Method 2: Giving C-Halogen;274
8.2.4.2.2.3;10.23.2.4.2.2.3 Method 3: Giving C-Oxygen;274
8.2.4.2.3;10.23.2.4.2.3 Modification of C-Carbon Functionalities;276
8.2.4.2.3.1;10.23.2.4.2.3.1 Method 1: Giving C-Carbon 9H-Pyrido[3,4-b]indoles;276
8.2.4.2.3.1.1;10.23.2.4.2.3.1.1 Variation 1: From Alkyl-Substituted 9H-Pyrido[3,4-b]indoles;276
8.2.4.2.3.1.2;10.23.2.4.2.3.1.2 Variation 2: From 9H-Pyrido[3,4-b]indolyl Alcohols;277
8.2.4.2.3.1.3;10.23.2.4.2.3.1.3 Variation 3: From 9H-Pyrido[3,4-b]indolyl Aldehydes and Ketones;278
8.2.4.2.3.1.4;10.23.2.4.2.3.1.4 Variation 4: From 9H-Pyrido[3,4-b]indole Acids, Esters, and Amides;279
8.2.4.2.3.2;10.23.2.4.2.3.2 Method 2: Giving C-Nitrogen 9H-Pyrido[3,4-b]indoles;281
8.2.4.2.3.3;10.23.2.4.2.3.3 Method 3: Giving C-Hydrogen 9H-Pyrido[3,4-b]indoles;283
8.3;10.23.3 Product Subclass 3: 5H-Pyrido[4,3-b]indoles (?-Carbolines);283
8.3.1;10.23.3.1 Synthesis by Ring-Closure Reactions;283
8.3.1.1;10.23.3.1.1 By Annulation to an Arene;283
8.3.1.1.1;10.23.3.1.1.1 By Formation of One N–C and Two C–C Bonds;283
8.3.1.1.1.1;10.23.3.1.1.1.1 With Formation of 1–2, 3–4, and 4a–9b Bonds;283
8.3.1.1.1.1.1;10.23.3.1.1.1.1.1 Method 1: From 2,N-Dialkynyl-N-tosylanilines and Methyl Cyanoformate;283
8.3.1.1.2;10.23.3.1.1.2 By Formation of One N–C Bond and One C–C Bond;284
8.3.1.1.2.1;10.23.3.1.1.2.1 With Formation of 4a–5 and 9a–9b Bonds;284
8.3.1.1.2.1.1;10.23.3.1.1.2.1.1 Method 1: From Arylhydrazines;284
8.3.1.1.2.1.1.1;10.23.3.1.1.2.1.1.1 Variation 1: Using a 4-Hydroxypyridin-2-one;284
8.3.1.1.2.1.1.2;10.23.3.1.1.2.1.1.2 Variation 2: Using 1-Acetyl-3-bromopiperidin-4-one;285
8.3.1.1.2.1.2;10.23.3.1.1.2.1.2 Method 2: From 4-Fluoro-3-iodopyridine;286
8.3.1.1.2.2;10.23.3.1.1.2.2 With Formation of 1–2 and 1–9b Bonds;287
8.3.1.1.2.2.1;10.23.3.1.1.2.2.1 Method 1: From Iminophosphoranes;287
8.3.1.1.3;10.23.3.1.1.3 By Formation of One N–C Bond;289
8.3.1.1.3.1;10.23.3.1.1.3.1 With Formation of the 4a–5 Bond;289
8.3.1.1.3.1.1;10.23.3.1.1.3.1.1 Method 1: From 3-(2-Azidoaryl)pyridines;289
8.3.1.1.3.1.1.1;10.23.3.1.1.3.1.1.1 Variation 1: From 3-(2-Azidoaryl)pyridinium Salts and a Ruthenium Catalyst;289
8.3.1.1.3.1.2;10.23.3.1.1.3.1.2 Method 2: From 3-(2-Nitrosoaryl)pyridines;291
8.3.1.1.3.1.3;10.23.3.1.1.3.1.3 Method 3: From 2-(3-Pyridyl)-N-tosylanilines or N-Acetyl-2-(3-pyridyl)-anilines;291
8.3.1.1.3.1.4;10.23.3.1.1.3.1.4 Method 4: From 4-Fluoro-3-(2-pivaloylaminophenyl)pyridine;292
8.3.1.1.4;10.23.3.1.1.4 By Formation of One C–C Bond;293
8.3.1.1.4.1;10.23.3.1.1.4.1 With Formation of the 9a–9b Bond;293
8.3.1.1.4.1.1;10.23.3.1.1.4.1.1 Method 1: From N-Arylpyridin-4-amines;293
8.3.1.1.4.1.2;10.23.3.1.1.4.1.2 Method 2: From an N-Arylpyridin-4-amine with at Least One Halogen on at Least One Ring;294
8.3.1.1.4.1.2.1;10.23.3.1.1.4.1.2.1 Variation 1: From an N-(2-Bromophenyl)pyridin-4-amine;294
8.3.1.1.4.1.2.2;10.23.3.1.1.4.1.2.2 Variation 2: From an N-Aryl-3-bromopyridin-4-amine;294
8.3.1.1.4.1.2.3;10.23.3.1.1.4.1.2.3 Variation 3: From an N-(2-Bromophenyl)-3-bromopyridin-4-amine by Palladium(0)-Catalyzed Bond Formation via Tributylstannyl Intermediates;295
8.3.1.1.4.1.3;10.23.3.1.1.4.1.3 Method 3: From N-Aryl-3-halopyridin-4-amines by Photostimulated SRN1 Reactions;296
8.3.1.2;10.23.3.1.2 By Annulation to a Heterocycle;296
8.3.1.2.1;10.23.3.1.2.1 By Annulation to a Pyridine;296
8.3.1.2.2;10.23.3.1.2.2 By Annulation to an Indole;297
8.3.1.2.2.1;10.23.3.1.2.2.1 By Formation of Two N–C and One C–C Bonds;297
8.3.1.2.2.1.1;10.23.3.1.2.2.1.1 With Formation of 1–2, 2–3, and 4–4a Bonds;297
8.3.1.2.2.1.1.1;10.23.3.1.2.2.1.1.1 Method 1: From 3-Acetyl-1H-indole, an Alkyne and a Primary Amine;297
8.3.1.2.2.1.2;10.23.3.1.2.2.1.2 With Formation of 1–2, 2–3, and 3–4 Bonds;298
8.3.1.2.2.1.2.1;10.23.3.1.2.2.1.2.1 Method 1: From 2-(2-Oxoalkyl)-1H-indole-3-carbaldehydes and Aryl Aldehydes;298
8.3.1.2.2.2;10.23.3.1.2.2.2 By Formation of Two N–C Bonds;299
8.3.1.2.2.2.1;10.23.3.1.2.2.2.1 With Formation of 1–2 and 2–3 Bonds;299
8.3.1.2.2.2.1.1;10.23.3.1.2.2.2.1.1 Method 1: From 2-(3-Acetyl-1H-indol-2-yl)acetonitrile;299
8.3.1.2.2.2.1.2;10.23.3.1.2.2.2.1.2 Method 2: From 2-(3-Formyl-1H-indol-2-yl)acrylates;300
8.3.1.2.2.2.1.2.1;10.23.3.1.2.2.2.1.2.1 Variation 1: From a 2-Alkynyl-1H-indole-3-carbaldehyde;301
8.3.1.2.2.2.1.2.2;10.23.3.1.2.2.2.1.2.2 Variation 2: From a 2-Alkenyl-1H-indole-3-carbaldehyde;301
8.3.1.2.2.2.1.3;10.23.3.1.2.2.2.1.3 Method 3: From (3-Acyl-1H-indol-2-yl)malonates;302
8.3.1.2.2.3;10.23.3.1.2.2.3 By Formation of One N–C Bond and One C–C Bond;304
8.3.1.2.2.3.1;10.23.3.1.2.2.3.1 With Formation of 2–3 and 3–4 Bonds;304
8.3.1.2.2.3.1.1;10.23.3.1.2.2.3.1.1 Method 1: From Secondary 2-Alkyl-1H-indole-3-carboxamides;304
8.3.1.2.2.3.2;10.23.3.1.2.2.3.2 With Formation of 2–3 and 4–4a Bonds;306
8.3.1.2.2.3.2.1;10.23.3.1.2.2.3.2.1 Method 1: From Oxime O-Methyl Ethers of 1H-Indol-3-yl Aldehydes or Ketones;306
8.3.1.2.2.3.2.1.1;10.23.3.1.2.2.3.2.1.1 Variation 1: Reaction with Alkynes and Alkenes;306
8.3.1.2.2.3.2.1.2;10.23.3.1.2.2.3.2.1.2 Variation 2: Reaction with Diphenylacetylene under Rhodium Catalysis;308
8.3.1.2.2.3.2.2;10.23.3.1.2.2.3.2.2 Method 2: From Tosylhydrazones of 1H-Indol-3-yl Aldehydes and Ketones;308
8.3.1.2.2.3.2.3;10.23.3.1.2.2.3.2.3 Method 3: From tert-Butylimines of 1H-Indole-3-carbaldehydes;310
8.3.1.2.2.3.2.3.1;10.23.3.1.2.2.3.2.3.1 Variation 1: From tert-Butylimines of 2-Halo-1H-indole-3-carbaldehydes;310
8.3.1.2.2.3.2.3.2;10.23.3.1.2.2.3.2.3.2 Variation 2: From tert-Butylimines of 2-Unsubstituted 1H-Indole-3-carbaldehydes;312
8.3.1.2.2.3.2.4;10.23.3.1.2.2.3.2.4 Method 4: From N-Methoxy or N-Alkyl/Aryl 1-Methyl-1H-indole-3-carboxamides;313
8.3.1.2.2.4;10.23.3.1.2.2.4 By Formation of Two C–C Bonds;314
8.3.1.2.2.4.1;10.23.3.1.2.2.4.1 With Formation of 1–9b and 4–4a Bonds;314
8.3.1.2.2.4.1.1;10.23.3.1.2.2.4.1.1 Method 1: From Triethyl 1,2,4-Triazine-3,5,6-tricarboxylate;314
8.3.1.2.2.5;10.23.3.1.2.2.5 By Formation of One N–C Bond;315
8.3.1.2.2.5.1;10.23.3.1.2.2.5.1 With Formation of the 1–2 Bond;315
8.3.1.2.2.5.1.1;10.23.3.1.2.2.5.1.1 Method 1: From a 3-Methyl-1H-indole-2-carbaldehyde;315
8.3.1.2.2.5.2;10.23.3.1.2.2.5.2 With Formation of the 2–3 Bond;316
8.3.1.2.2.5.2.1;10.23.3.1.2.2.5.2.1 Method 1: From a 3-Acyl-2-alkenyl-1H-indole Oxime;316
8.3.1.2.2.5.2.2;10.23.3.1.2.2.5.2.2 Method 2: From tert-Butylimines of 2-Alkynyl-1H-indole-3-carbaldehydes;317
8.3.1.2.2.6;10.23.3.1.2.2.6 By Formation of One C–C Bond;319
8.3.1.2.2.6.1;10.23.3.1.2.2.6.1 With Formation of the 4–4a Bond;319
8.3.1.2.2.6.1.1;10.23.3.1.2.2.6.1.1 Method 1: From 3-{[(2,2-Diethoxyethyl)imino]methyl}-1H-indoles;319
8.3.1.2.2.6.1.1.1;10.23.3.1.2.2.6.1.1.1 Variation 1: From 3-{[(2,2-Diethoxyethyl)amino]methyl}-1H-indoles;320
8.3.1.2.2.6.1.2;10.23.3.1.2.2.6.1.2 Method 2: From Ethyl [(1H-Indol-3-yl)methyl]glycinates;321
8.3.1.2.2.6.1.3;10.23.3.1.2.2.6.1.3 Method 3: From N-Allyl-2-iodo-1H-indole-3-carboxamides;322
8.3.2;10.23.3.2 Synthesis by Ring Transformation;323
8.3.2.1;10.23.3.2.1 Method 1: From 1-(4-Pyridyl)-1H-benzotriazoles;323
8.3.2.2;10.23.3.2.2 Method 2: From 1-Aryl-1H-1,2,3-triazolo[4,5-c]pyridines;325
8.3.2.3;10.23.3.2.3 Method 3: By Ring Expansion of 5-Azidocyclopent-2-en-1-ols To Form Pyridines;325
8.3.3;10.23.3.3 Aromatization;326
8.3.3.1;10.23.3.3.1 Method 1: From Tetrahydro-5H-pyrido[4,3-b]indoles and Octahydro-5H-pyrido[4,3-b]indoles;326
8.3.3.2;10.23.3.3.2 Method 2: From Dihydro-5H-pyrido[4,3-b]indoles;330
8.3.4;10.23.3.4 Synthesis by Substituent Modification;333
8.3.4.1;10.23.3.4.1 Substitution of Existing Substituents;333
8.3.4.1.1;10.23.3.4.1.1 Substitution of N-Hydrogen;333
8.3.4.1.1.1;10.23.3.4.1.1.1 Giving N-Sulfur 5H-Pyrido[4,3-b]indoles;333
8.3.4.1.1.2;10.23.3.4.1.1.2 Giving N-Carbon 5H-Pyrido[4,3-b]indoles;334
8.3.4.1.1.2.1;10.23.3.4.1.1.2.1 Method 1: 5-Alkylation Using an Alkyl Halide;334
8.3.4.1.1.2.2;10.23.3.4.1.1.2.2 Method 2: 5-Arylation Using an Aryl Halide;336
8.3.4.1.1.2.3;10.23.3.4.1.1.2.3 Method 3: 2-Alkylation Giving 2-Alkyl-5H-pyrido[4,3-b]indol-2-ium Salts and thence 5-Alkylation;336
8.3.4.1.2;10.23.3.4.1.2 Substitution of N-Carbon and N-Sulfur;338
8.3.4.1.2.1;10.23.3.4.1.2.1 Giving N-Hydrogen 5H-Pyrido[4,3-b]indoles;338
8.3.4.1.2.1.1;10.23.3.4.1.2.1.1 Method 1: N-Deprotection;338
8.3.4.1.3;10.23.3.4.1.3 Substitution of C-Hydrogen;339
8.3.4.1.3.1;10.23.3.4.1.3.1 Direct Substitution by Electrophiles;339
8.3.4.1.3.1.1;10.23.3.4.1.3.1.1 Method 1: Giving C-Halogen;339
8.3.4.1.3.1.2;10.23.3.4.1.3.1.2 Method 2: Giving C-Sulfur;339
8.3.4.1.3.1.3;10.23.3.4.1.3.1.3 Method 3: Giving C-Nitrogen;340
8.3.4.1.3.1.4;10.23.3.4.1.3.1.4 Method 4: Giving C-Carbon;340
8.3.4.1.3.2;10.23.3.4.1.3.2 Substitution via Metalation;341
8.3.4.1.3.3;10.23.3.4.1.3.3 Substitution via 2-Oxides;342
8.3.4.1.3.4;10.23.3.4.1.3.4 Substitution via Displacement of Halogen;344
8.3.4.1.3.4.1;10.23.3.4.1.3.4.1 Method 1: Direct Nucleophilic Displacement;344
8.3.4.1.3.4.2;10.23.3.4.1.3.4.2 Method 2: Substitution of Halogen via Cross-Coupling Processes;347
8.3.4.2;10.23.3.4.2 Modification of Substituents;350
8.3.4.2.1;10.23.3.4.2.1 Modification of C-Oxygen Functionalities;350
8.3.4.2.1.1;10.23.3.4.2.1.1 Method 1: Giving C-Halogen;350
8.3.4.2.2;10.23.3.4.2.2 Modification of C-Nitrogen Functionalities;351
8.3.4.2.2.1;10.23.3.4.2.2.1 Method 1: Giving C-Nitrogen;351
8.3.4.2.3;10.23.3.4.2.3 Modification of C-Carbon Functionalities;351
8.3.4.2.3.1;10.23.3.4.2.3.1 Method 1: Giving C-Carbon 5H-Pyrido[4,3-b]indoles;351
8.3.4.2.3.2;10.23.3.4.2.3.2 Method 2: Giving C-Nitrogen 5H-Pyrido[4,3-b]indoles;352
8.3.4.2.3.3;10.23.3.4.2.3.3 Method 3: Giving C-Hydrogen 5H-Pyrido[4,3-b]indoles;352
8.4;10.23.4 Product Subclass 4: 5H-Pyrido[3,2-b]indoles (?-Carbolines);353
8.4.1;10.23.4.1 Synthesis by Ring-Closure Reactions;353
8.4.1.1;10.23.4.1.1 By Annulation to an Arene;353
8.4.1.1.1;10.23.4.1.1.1 By Formation of One N–C and Two C–C Bonds;353
8.4.1.1.1.1;10.23.4.1.1.1.1 With Formation of 2–3, 4a–5, and 9a–9b Bonds;353
8.4.1.1.1.1.1;10.23.4.1.1.1.1.1 Method 1: From 2-Iodoanilines and N-Tosyl Enynamines;353
8.4.1.1.2;10.23.4.1.1.2 By Formation of Two N–C Bonds;354
8.4.1.1.2.1;10.23.4.1.1.2.1 With Formation of 4a–5 and 5–5a Bonds;354
8.4.1.1.2.1.1;10.23.4.1.1.2.1.1 Method 1: From Primary Amines and 3-Bromo-2-(2-bromophenyl)pyridine;354
8.4.1.1.3;10.23.4.1.1.3 By Formation of Two C–C Bonds;355
8.4.1.1.3.1;10.23.4.1.1.3.1 With Formation of 2–3 and 4a–9b Bonds;355
8.4.1.1.3.1.1;10.23.4.1.1.3.1.1 Method 1: From 2-(Aminomethyl)aniline Cinnamaldehyde Diimine;355
8.4.1.1.4;10.23.4.1.1.4 By Formation of One N–C Bond;356
8.4.1.1.4.1;10.23.4.1.1.4.1 With Formation of the 4a–5 Bond;356
8.4.1.1.4.1.1;10.23.4.1.1.4.1.1 Method 1: From 1-Methyl-2-(2-Azidoaryl)pyridinium Trifluoromethanesulfonates;356
8.4.1.1.4.1.2;10.23.4.1.1.4.1.2 Method 2: From 3-Fluoro-2-[2-(pivaloylamino)phenyl]pyridines;357
8.4.1.1.4.2;10.23.4.1.1.4.2 With Formation of the 5–5a Bond;359
8.4.1.1.4.2.1;10.23.4.1.1.4.2.1 Method 1: From 3-Azido-2-phenylpyridine;359
8.4.1.1.4.2.2;10.23.4.1.1.4.2.2 Method 2: From 2-Aryl-3-nitropyridines;360
8.4.1.1.4.2.3;10.23.4.1.1.4.2.3 Method 3: From 2-(2-Chlorophenyl)pyridin-3-amine by Intramolecular Photostimulated SRN1 Reaction;361
8.4.1.1.5;10.23.4.1.1.5 By Formation of One C–C Bond;362
8.4.1.1.5.1;10.23.4.1.1.5.1 With Formation of the 9a–9b Bond;362
8.4.1.1.5.1.1;10.23.4.1.1.5.1.1 Method 1: From N-Arylpyridin-3-amines by Irradiation;362
8.4.1.1.5.1.2;10.23.4.1.1.5.1.2 Method 2: From N-Arylpyridin-3-amines by Palladium(0)-Catalyzed Bond Formation;363
8.4.1.1.5.1.2.1;10.23.4.1.1.5.1.2.1 Variation 1: From Cyclohexanone and Pyridin-3-amine;364
8.4.1.1.5.1.3;10.23.4.1.1.5.1.3 Method 3: From N-(2-Halophenyl)pyridin-3-amines by Palladium(0)-Catalyzed Bond Formation;364
8.4.1.1.5.1.4;10.23.4.1.1.5.1.4 Method 4: From N-Aryl-2-halopyridin-3-amines by Intramolecular Palladium(0)-Catalyzed Bond Formation;365
8.4.1.1.5.1.5;10.23.4.1.1.5.1.5 Method 5: From N-Aryl-2-bromopyridin-3-amines by Intramolecular Photostimulated SRN1 Reaction;367
8.4.1.1.5.1.6;10.23.4.1.1.5.1.6 Method 6: From 2-Bromo-N-(2-bromophenyl)pyridin-3-amines by Palladium(0)-Catalyzed Bond Formation via Tributylstannyl Intermediates;367
8.4.1.1.5.1.7;10.23.4.1.1.5.1.7 Method 7: From an N-(2-Diazophenyl)-N-methylpyridin-3-amine;368
8.4.1.2;10.23.4.1.2 By Annulation to a Heterocycle;368
8.4.1.2.1;10.23.4.1.2.1 By Annulation to a Pyridine;368
8.4.1.2.1.1;10.23.4.1.2.1.1 By Formation of One N–C Bond and One C–C Bond;368
8.4.1.2.1.1.1;10.23.4.1.2.1.1.1 With Formation of 5–5a and 9a–9b Bonds;368
8.4.1.2.1.1.1.1;10.23.4.1.2.1.1.1.1 Method 1: From Benzyne and an N-Tosylpyridinium Imide;368
8.4.1.2.2;10.23.4.1.2.2 By Annulation to an Indole;370
8.4.1.2.2.1;10.23.4.1.2.2.1 By Formation of One N–C and Two C–C Bonds;370
8.4.1.2.2.1.1;10.23.4.1.2.2.1.1 With Formation of 1–9b, 2–3, and 4–4a Bonds;370
8.4.1.2.2.1.1.1;10.23.4.1.2.2.1.1.1 Method 1: From 3-Acetyl-1H-indole Oxime and Acetylene;370
8.4.1.2.2.1.2;10.23.4.1.2.2.1.2 With Formation of 1–2, 2–3, and 4–4a Bonds;371
8.4.1.2.2.1.2.1;10.23.4.1.2.2.1.2.1 Method 1: From N-(tert-Butoxycarbonyl)indol-3-amines, Aryl Aldehydes, and Terminal Arylalkynes;371
8.4.1.2.2.2;10.23.4.1.2.2.2 By Formation of One N–C Bond and One C–C Bond;373
8.4.1.2.2.2.1;10.23.4.1.2.2.2.1 With Formation of 1–9b and 3–4 Bonds;373
8.4.1.2.2.2.1.1;10.23.4.1.2.2.2.1.1 Method 1: From 2-[Bis(methylsulfanyl)methylene]-1-methyl-1,3-dihydro-2H-indol-3-one and a ß-(Lithioamino)acrylonitrile;373
8.4.1.2.2.2.1.1.1;10.23.4.1.2.2.2.1.1.1 Variation 1: From 2-[Bis(methylsulfanyl)methylene]-1-methyl-1,3-dihydro-2H-indol-3-one and Malononitrile;374
8.4.1.2.2.2.2;10.23.4.1.2.2.2.2 With Formation of 1–2 and 4–4a Bonds;374
8.4.1.2.2.2.2.1;10.23.4.1.2.2.2.2.1 Method 1: From an N-Acetyl-1H-indol-3-amine and a 1,3-Dialdehyde Equivalent;374
8.4.1.2.3;10.23.4.1.2.3 By Annulation to a 1H-Pyrrolo[3,2-b]pyridine (a 4-Azaindole);375
8.4.1.2.3.1;10.23.4.1.2.3.1 By Formation of Two C–C Bonds;375
8.4.1.2.3.1.1;10.23.4.1.2.3.1.1 With Formation of 7–8 and 9–9a Bonds;375
8.4.1.2.3.1.1.1;10.23.4.1.2.3.1.1.1 Method 1: From a 2-Vinyl-1H-Pyrrolo[3,2-b]pyridine and Dimethyl Acetylenedicarboxylate;375
8.4.2;10.23.4.2 Synthesis by Ring Transformation;376
8.4.2.1;10.23.4.2.1 Method 1: From 1-(3-Pyridyl)-1H-benzotriazoles;376
8.4.2.2;10.23.4.2.2 Method 2: From 2-Alkoxypyrano[3,2-b]indoles and Hydroxylamine;376
8.4.3;10.23.4.3 Aromatization;377
8.4.4;10.23.4.4 Synthesis by Substituent Modification;379
8.4.4.1;10.23.4.4.1 Substitution of Existing Substituents;379
8.4.4.1.1;10.23.4.4.1.1 Substitution of N-Hydrogen;379
8.4.4.1.1.1;10.23.4.4.1.1.1 Giving N-Carbon 5H-Pyrido[3,2-b]indoles;379
8.4.4.1.1.1.1;10.23.4.4.1.1.1.1 Method 1: Using an Alkyl Halide and Sodium Hydride;379
8.4.4.1.1.1.2;10.23.4.4.1.1.1.2 Method 2: Demethylation of a 1-Methyl-5H-pyrido[3,2-b]indol-1-ium Iodide;380
8.4.4.1.1.1.3;10.23.4.4.1.1.1.3 Method 3: 5-Arylation Using an Aryl Halide;383
8.4.4.1.2;10.23.4.4.1.2 Substitution of C-Hydrogen;384
8.4.4.1.2.1;10.23.4.4.1.2.1 Substitution by Electrophiles;384
8.4.4.1.2.1.1;10.23.4.4.1.2.1.1 Method 1: Giving C-Nitrogen 5H-Pyrido[3,2-b]indoles;384
8.4.4.1.2.2;10.23.4.4.1.2.2 Substitution via Metalation;385
8.4.4.2;10.23.4.4.2 Modification of Substituents;386
8.4.4.2.1;10.23.4.4.2.1 Modification of C-Carbon Functionalities;386
8.4.4.2.1.1;10.23.4.4.2.1.1 Method 1: Giving C-Nitrogen 5H-Pyrido[3,2-b]indoles;386
8.4.4.2.1.2;10.23.4.4.2.1.2 Method 2: Giving C-Carbon 5H-Pyrido[3,2-b]indoles;386
9;30.3 Product Class 3: S, S-Acetals;401
10;30.3.2.2 1,3-Dithietanes;415
10.1;30.3.2.2.1 Symmetrical Dithietanes;415
10.1.1;30.3.2.2.1.1 Method 1: Dimerization of Thioketones Formed In Situ from Bunte Salts;415
10.1.2;30.3.2.2.1.2 Method 2: Synthesis from Thiophosgene: Dimerization of Thiocarbonates;416
10.1.3;30.3.2.2.1.3 Method 3: Dimerization of Thioacetamides;417
10.2;30.3.2.2.2 Unsymmetrical Dithietanes;417
10.2.1;30.3.2.2.2.1 Method 1: Synthesis from Thioketones and Imines;417
10.2.2;30.3.2.2.2.2 Method 2: Synthesis from Aromatic Aldehydes and Carbon Disulfide;418
10.2.3;30.3.2.2.2.3 Method 3: Synthesis of Dithietane Cations;419
11;30.3.3.2 1,3-Dithiolanes;421
11.1;30.3.3.2.1 Method 1: Reaction of Ethane-1,2-dithiol with Aldehydes or Ketones Catalyzed by Protic Acids;421
11.1.1;30.3.3.2.1.1 Variation 1: Catalyzed by Hydrogen Chloride;421
11.1.2;30.3.3.2.1.2 Variation 2: Catalyzed by 4-Toluenesulfonic Acid;422
11.1.3;30.3.3.2.1.3 Variation 3: Catalyzed by Sulfuric Acid on Silica Gel;422
11.1.4;30.3.3.2.1.4 Variation 4: Catalyzed by Alumina Sulfuric Acid, Silica Sulfuric Acid, and Tungstate Sulfuric Acid;423
11.1.5;30.3.3.2.1.5 Variation 5: Catalyzed by Sulfamic Acid on Silica Gel;427
11.1.6;30.3.3.2.1.6 Variation 6: Catalyzed by Sulfonic Acids on Solid Supports and Ionic Liquids;428
11.1.7;30.3.3.2.1.7 Variation 7: Catalyzed by Sodium Hydrogen Sulfate on Silica Gel;431
11.1.8;30.3.3.2.1.8 Variation 8: Catalyzed by Solid-Supported Perchloric Acid;432
11.1.9;30.3.3.2.1.9 Variation 9: Catalyzed by Trichloroacetic Acid in Sodium Dodecyl Sulfate Micelles;432
11.2;30.3.3.2.2 Method 2: Reactions of Ethane-1,2-dithiol with Aldehydes or Ketones Catalyzed by Lewis Acids;433
11.2.1;30.3.3.2.2.1 Variation 1: Catalyzed by Boron-Based Reagents;433
11.2.2;30.3.3.2.2.2 Variation 2: Catalyzed by Aluminum Chloride and Related Reagents;435
11.2.3;30.3.3.2.2.3 Variation 3: Catalyzed by Indium(III) Reagents;437
11.2.4;30.3.3.2.2.4 Variation 4: Catalyzed by Silicon-Based Reagents;439
11.2.5;30.3.3.2.2.5 Variation 5: Catalyzed by Tin-Based Reagents;440
11.2.6;30.3.3.2.2.6 Variation 6: Catalyzed by Titanium-Based Reagents;441
11.2.7;30.3.3.2.2.7 Variation 7: Catalyzed by Vanadium-Based Reagents;442
11.2.8;30.3.3.2.2.8 Variation 8: Catalyzed by Iron-Based Reagents;444
11.2.9;30.3.3.2.2.9 Variation 9: Catalyzed by Ruthenium-Based Reagents;446
11.2.10;30.3.3.2.2.10 Variation 10: Catalyzed by Nickel-Based Reagents;448
11.2.11;30.3.3.2.2.11 Variation 11: Promoted by Copper-Based Reagents;449
11.2.12;30.3.3.2.2.12 Variation 12: Catalyzed by Zinc-Based Reagents;450
11.2.13;30.3.3.2.2.13 Variation 13: Catalyzed by Hafnium-Based Reagents;451
11.3;30.3.3.2.3 Method 3: Reaction of Ethane-1,2-dithiol with Aldehydes or Ketones Catalyzed by Heterogeneous Catalysts;452
11.3.1;30.3.3.2.3.1 Variation 1: Catalyzed by Phosphorus Pentoxide on Alumina and Silica Gel Reagents;452
11.3.2;30.3.3.2.3.2 Variation 2: Using Dithiolanylium Tetrafluoroborate Salts on Solid Support;455
11.3.3;30.3.3.2.3.3 Variation 3: Catalyzed by Graphene Oxide;456
11.4;30.3.3.2.4 Method 4: Reaction of Ethane-1,2-dithiol with Aldehydes or Ketones Catalyzed by Halogens and Derivatives;457
11.4.1;30.3.3.2.4.1 Variation 1: Catalyzed by Iodine;457
11.4.2;30.3.3.2.4.2 Variation 2: Catalyzed by Tribromide Salts;459
11.4.3;30.3.3.2.4.3 Variation 3: Catalyzed by N-Bromosuccinimide;461
11.4.4;30.3.3.2.4.4 Variation 4: Catalyzed by Poly(N-bromoacrylamide);462
11.4.5;30.3.3.2.4.5 Variation 5: Catalyzed by N,N,N',N'-Tetrabromobenzene-1,3-disulfonamide and Poly(ethylene-N,N'-dibromobenzene-1,3-disulfonamide);463
11.4.6;30.3.3.2.4.6 Variation 6: Catalyzed by Trichloromelamine;464
11.5;30.3.3.2.5 Method 5: Reaction of Ethane-1,2-dithiol with Aldehydes or Ketones Catalyzed by Ionic Liquids;465
11.5.1;30.3.3.2.5.1 Variation 1: Catalyzed by Iminium Salts Structurally Similar to Ionic Liquids;465
11.6;30.3.3.2.6 Method 6: Reaction of Ethane-1,2-dithiol with Masked Carbonyl Groups;467
11.6.1;30.3.3.2.6.1 Variation 1: Conversion of (E)-2-Chlorovinyl Sulfones into 1,3-Dithiolane Derivatives;467
11.6.2;30.3.3.2.6.2 Variation 2: One-Pot Conversion of Ethoxyacetylene, an a,ß-Unsaturated Aldehyde, and Ethane-1,2-dithiol into a 2-(Buta-1,3-dienyl)-1,3-dithiolane;467
11.7;30.3.3.2.7 Method 7: Reaction of O,O-Acetals or Hemiacetals with Ethane-1,2-dithiol;468
11.7.1;30.3.3.2.7.1 Variation 1: Catalyzed by Protic Acids;468
11.7.2;30.3.3.2.7.2 Variation 2: Catalyzed by Lewis Acids;471
11.7.3;30.3.3.2.7.3 Variation 3: Catalyzed by Heterogeneous Catalysts;473
11.7.4;30.3.3.2.7.4 Variation 4: Catalyzed by Halogens and Derivatives;474
11.8;30.3.3.2.8 Method 8: Dithioacetalization from a 1,3-Dithiolane to Another Carbonyl Group;476
11.9;30.3.3.2.9 Method 9: Addition of Ethane-1,2-dithiol to Alkynes;477
11.9.1;30.3.3.2.9.1 Variation 1: Gold(I)/Silver(I) Tetrafluoroborate Catalyzed Bishydrothiolation of Alkynes;477
11.9.2;30.3.3.2.9.2 Variation 2: Calcium Nonafluorobutane-1-sulfonate Catalyzed anti-Markovnikov Bishydrothiolation of Alkynes;477
11.9.3;30.3.3.2.9.3 Variation 3: Double Michael Addition of Ethane-1,2-dithiol to Propargylic Carbonyl Systems;478
11.10;30.3.3.2.10 Method 10: Metalation;481
11.10.1;30.3.3.2.10.1 Variation 1: 2-(Trimethylsilyl)-1,3-dithiolanes as Masked 1,3-Dithiolane Anions;482
11.11;30.3.3.2.11 Method 11: Annulation;483
11.11.1;30.3.3.2.11.1 Variation 1: Tandem Hydride Shift/Cyclization;483
11.11.2;30.3.3.2.11.2 Variation 2: [6 + 3] Cycloaddition;484
11.11.3;30.3.3.2.11.3 Variation 3: [4 + 2] Cycloaddition;485
11.12;30.3.3.2.12 Method 12: Metal-Free Cross-Dehydrogenative Coupling of 1H-Benzimidazoles with 1,3-Dithiolane;486
11.13;30.3.3.2.13 Method 13: Reduction of Ketene S,S-Acetals;487
11.14;30.3.3.2.14 Method 14: [3 + 2] Cycloaddition of Ketene S,S-Acetals;488
11.15;30.3.3.2.15 Method 15: Intramolecular Cyclization of Ketene S,S-Acetals;489
11.15.1;30.3.3.2.15.1 Variation 1: Nazarov Cyclization–Halovinylation of a-Alkenoyl Ketene S,S-Acetals;489
11.15.2;30.3.3.2.15.2 Variation 2: Intramolecular Michael Reaction;490
11.16;30.3.3.2.16 Method 16: Double-Bond Migration in Ketene S,S-Acetals;491
12;Author Index;497
13;Abbreviations;517
