Indole Ring Synthesis - From Natural Products to Drug Discovery

Informationen zum Autor Professor Gordon Gribble, Department of Chemistry, Dartmouth College, USA Professor Gribble has been the co-editor of the annual book series Progress in Heterocyclic Chemistry for the past 10 years. His research programs involve several areas of organic chemistry, most of which involve synthesis: biologically active natural products, novel indole chemistry, anticancer triterpenoid synthesis, new synthetic methodology, and novel radical and cycloaddition chemistry of heterocycles. Klappentext Of the myriad of heterocycles known to man, the indole ring stands foremost for its remarkably versatile chemistry, its enormous range of biological activities, and its ubiquity in the terrestrial and marine environments.The indole ring continues to be discovered in natural products and to be employed in man-made pharmaceuticals and other materials. Given the enormous resurgence in indole ring synthesis over the past decade -- highlighted by the power of transition metal catalysis -- this authoritative guide addresses the need for a comprehensive presentation of the myriad of methods for constructing the indole ring, from the ancient to the modern, and from the obscure to the well-known.Following presentation of the classic indole ring syntheses and many newer methods, coverage continues with indole ring syntheses via pyrroles, indolines, oxindoles, isatins, radical and photochemical reactions, aryne cycloadditions. This extensive volume concludes with the modern transition metal-catalyzed indole ring syntheses that utilize copper, palladium, rhodium, gold, ruthenium, platinum, and other metals to fashion the indole ringIndole Ring Synthesis is a comprehensive, authoritative and up-to-date guide to the synthesis of this important heterocycle for organic chemists, pharmaceutical researchers and those interested in the chemistry of natural products. Zusammenfassung Of the myriad of heterocycles known to man, the indole ring stands foremost for its remarkably versatile chemistry, its enormous range of biological activities, and its ubiquity in the terrestrial and marine environments. Inhaltsverzeichnis 1 Introduction 1 1.1 Preview 1 1.2 Indole¿Containing Natural Products 1 1.3 Biological Activity of Indoles 4 1.4 Indole¿Containing Pharmaceuticals 15 1.5 Indole¿Containing Materials 21 1.6 Indole¿Containing Ligands 28 1.7 Reviews of Indole¿Ring Synthesis 32 1.7.1 General Reviews on Indole Ring Synthesis 32 1.7.2 Specialized Reviews 32 1.7.3 Name Reactions 33 1.7.4 Miscellaneous Reviews 33 1.7.5 Synthesis of Carbazoles, Carbolines, and Indolocarbazoles 34 1.7.6 Reviews of Indole Analogues 34 References 34 PART I Sigmatropic Rearrangements 39 2 Fischer Indole Synthesis 41 2.1 Preview 41 2.2 Methods 41 2.2.1 Traditional Methods 41 2.2.2 Metal¿Catalyzed Methods 44 2.2.3 Solid¿Phase Fischer Indolization Method 56 2.2.4 Other General Methods 57 2.2.5 Hydrazones 63 2.2.6 Other Variations of Fischer Indole Synthesis 66 2.3 Applications of Fischer Indolizations 68 2.3.1 Drug Targets 68 2.3.2 Natural Products 82 2.3.3 Materials 97 2.3.4 General 98 References 108 3 Gassman Indole Synthesis 116 4 Bartoli Indole Synthesis 121 5 Thyagarajan Indole Synthesis 131 6 Julia Indole Synthesis 137 7 Miscellaneous Sigmatropic Rearrangements 139 PART II Nucleophilic Cyclization 145 8 Madelung Indole Synthesis 147 9 Wittig-Madelung Indole Synthesis 156 10 Jones-Schmid Indole Synthesis 165 11 Couture Indole Synthesis 174 12 Wender Indole Synthesis 176 13 Smith Indole Synthesis 181 14 Kihara Indole Synthesis 186 15 Nenitzescu 5¿Hydroxyindole Synthesis 188 16 Engler¿Kita...

List of contents

1 Introduction 1
 
1.1 Preview 1
 
1.2 Indole-Containing Natural Products 1
 
1.3 Biological Activity of Indoles 4
 
1.4 Indole-Containing Pharmaceuticals 15
 
1.5 Indole-Containing Materials 21
 
1.6 Indole-Containing Ligands 28
 
1.7 Reviews of Indole-Ring Synthesis 32
 
1.7.1 General Reviews on Indole Ring Synthesis 32
 
1.7.2 Specialized Reviews 32
 
1.7.3 Name Reactions 33
 
1.7.4 Miscellaneous Reviews 33
 
1.7.5 Synthesis of Carbazoles, Carbolines, and Indolocarbazoles 34
 
1.7.6 Reviews of Indole Analogues 34
 
References 34
 
PART I Sigmatropic Rearrangements 39
 
2 Fischer Indole Synthesis 41
 
2.1 Preview 41
 
2.2 Methods 41
 
2.2.1 Traditional Methods 41
 
2.2.2 Metal-Catalyzed Methods 44
 
2.2.3 Solid-Phase Fischer Indolization Method 56
 
2.2.4 Other General Methods 57
 
2.2.5 Hydrazones 63
 
2.2.6 Other Variations of Fischer Indole Synthesis 66
 
2.3 Applications of Fischer Indolizations 68
 
2.3.1 Drug Targets 68
 
2.3.2 Natural Products 82
 
2.3.3 Materials 97
 
2.3.4 General 98
 
References 108
 
3 Gassman Indole Synthesis 116
 
4 Bartoli Indole Synthesis 121
 
5 Thyagarajan Indole Synthesis 131
 
6 Julia Indole Synthesis 137
 
7 Miscellaneous Sigmatropic Rearrangements 139
 
PART II Nucleophilic Cyclization 145
 
8 Madelung Indole Synthesis 147
 
9 Wittig-Madelung Indole Synthesis 156
 
10 Jones-Schmid Indole Synthesis 165
 
11 Couture Indole Synthesis 174
 
12 Wender Indole Synthesis 176
 
13 Smith Indole Synthesis 181
 
14 Kihara Indole Synthesis 186
 
15 Nenitzescu 5-Hydroxyindole Synthesis 188
 
16 Engler-Kita Indole Synthesis 206
 
17 Bailey-Liebeskind-O'Shea Indoline-Indole Synthesis 213
 
18 Wright Indoline Synthesis 219
 
19 Saegusa Indole Synthesis 221
 
20 Ichikawa Indole Synthesis 228
 
21 Miscellaneous Nucleophilic Cyclizations that Form the Indole Ring 230
 
22 Sugasawa Indole Synthesis 244
 
PART III Electrophilic Cyclization 247
 
23 Bischler Indole Synthesis 249
 
24 The Nordlander Indole Synthesis 260
 
25 Nitrene Cyclization 264
 
26 Cadogan-Sundberg Indole Synthesis 266
 
27 Sundberg Indole Synthesis 278
 
28 Hemetsberger Indole Synthesis 287
 
29 Taber Indole Synthesis 296
 
30 Knochel Indole Synthesis 299
 
31 Täuber Carbazole Synthesis 301
 
32 Quéguiner Azacarbazole Synthesis 304
 
33 Iwao Indole Synthesis 307
 
34 Hewson Indole Synthesis 309
 
35 Magnus Indole Synthesis 310
 
36 Feldman Indole Synthesis 311
 
37 Butin Indole Synthesis 313
 
38 Miscellaneous Electrophilic Cyclizations 317
 
PART IV Reductive Cyclization 323
 
39 Nenitzescu o,ß-Dinitrostyrene Reductive Cyclization 325
 
40 Reissert Indole Synthesis 332
 
41 Leimgruber-Batcho Indole Synthesis 338
 
42 Pschorr-Hoppe Indole Synthesis 349
 
43 Mkosza Indole Synthesis 354
 
44 Rawal Indole Synthesis 361
 
45 The Baeyer-Jackson Indole Synthesis and Miscellaneous Reductive Cyclization Indole Syntheses 363
 
PART V Oxidative Cyclization 381
 
46 Watanabe Indole Synthesis 383
 
47 Knölker Carbazole Synthesis 391
 
48 Miscellaneous Oxidative Cyclizations 396
 
PART VI Radical Cyclization 403
 
49 Fukuyama Indole Synthesis 405
 
50 Othe

Product details

• Authors: G Gribble, Gordon Gribble, Gordon W Gribble, Gordon W. Gribble, Gordon W. (Dartmouth College) Gribble, Gribble Gordon W.
• Publisher: Wiley, John and Sons Ltd
• Languages: English
• Product format: Hardback
• Released: 05.08.2016
• EAN: 9780470512180
• ISBN: 978-0-470-51218-0
• No. of pages: 704
• Subjects: Natural sciences, medicine, IT, technology > Chemistry > Physical chemistry; Chemie, Organische Chemie, Wirkstoffforschung, chemistry, Natural Products, Naturstoffchemie, Wirkstoffforschung u. -entwicklung, Drug Discovery & Development, Pharmaceutical & Medicinal Chemistry, Pharmazeutische u. Medizinische Chemie, Methods - Synthesis & Techniques, Organische Chemie / Methoden, Synthesen, Verfahren, PHARMAZEUTISCHE CHEMIE