Indole Ring Synthesis

Professor Gordon Gribble, Department of Chemistry, Dartmouth College, USAProfessor 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.

• 1 Introduction 11.1 Preview 11.2 Indole‐Containing Natural Products 11.3 Biological Activity of Indoles 41.4 Indole‐Containing Pharmaceuticals 151.5 Indole‐Containing Materials 211.6 Indole‐Containing Ligands 281.7 Reviews of Indole‐Ring Synthesis 321.7.1 General Reviews on Indole Ring Synthesis 321.7.2 Specialized Reviews 321.7.3 Name Reactions 331.7.4 Miscellaneous Reviews 331.7.5 Synthesis of Carbazoles, Carbolines, and Indolocarbazoles 341.7.6 Reviews of Indole Analogues 34References 34PART I Sigmatropic Rearrangements 392 Fischer Indole Synthesis 412.1 Preview 412.2 Methods 412.2.1 Traditional Methods 412.2.2 Metal‐Catalyzed Methods 442.2.3 Solid‐Phase Fischer Indolization Method 562.2.4 Other General Methods 572.2.5 Hydrazones 632.2.6 Other Variations of Fischer Indole Synthesis 662.3 Applications of Fischer Indolizations 682.3.1 Drug Targets 682.3.2 Natural Products 822.3.3 Materials 972.3.4 General 98References 1083 Gassman Indole Synthesis 1164 Bartoli Indole Synthesis 1215 Thyagarajan Indole Synthesis 1316 Julia Indole Synthesis 1377 Miscellaneous Sigmatropic Rearrangements 139PART II Nucleophilic Cyclization 1458 Madelung Indole Synthesis 1479 Wittig–Madelung Indole Synthesis 15610 Jones–Schmid Indole Synthesis 16511 Couture Indole Synthesis 17412 Wender Indole Synthesis 17613 Smith Indole Synthesis 18114 Kihara Indole Synthesis 18615 Nenitzescu 5‐Hydroxyindole Synthesis 18816 Engler‐Kita Indole Synthesis 20617 Bailey–Liebeskind–O’Shea Indoline–Indole Synthesis 21318 Wright Indoline Synthesis 21919 Saegusa Indole Synthesis 22120 Ichikawa Indole Synthesis 22821 Miscellaneous Nucleophilic Cyclizations that Form the Indole Ring 23022 Sugasawa Indole Synthesis 244PART III Electrophilic Cyclization 24723 Bischler Indole Synthesis 24924 The Nordlander Indole Synthesis 26025 Nitrene Cyclization 26426 Cadogan–Sundberg Indole Synthesis 26627 Sundberg Indole Synthesis 27828 Hemetsberger Indole Synthesis 28729 Taber Indole Synthesis 29630 Knochel Indole Synthesis 29931 Täuber Carbazole Synthesis 30132 Quéguiner Azacarbazole Synthesis 30433 Iwao Indole Synthesis 30734 Hewson Indole Synthesis 30935 Magnus Indole Synthesis 31036 Feldman Indole Synthesis 31137 Butin Indole Synthesis 31338 Miscellaneous Electrophilic Cyclizations 317PART IV Reductive Cyclization 32339 Nenitzescu o,β‐Dinitrostyrene Reductive Cyclization 32540 Reissert Indole Synthesis 33241 Leimgruber–Batcho Indole Synthesis 33842 Pschorr–Hoppe Indole Synthesis 34943 Mąkosza Indole Synthesis 35444 Rawal Indole Synthesis 36145 The Baeyer–Jackson Indole Synthesis and Miscellaneous Reductive Cyclization Indole Syntheses 363PART V Oxidative Cyclization 38146 Watanabe Indole Synthesis 38347 Knölker Carbazole Synthesis 39148 Miscellaneous Oxidative Cyclizations 396PART VI Radical Cyclization 40349 Fukuyama Indole Synthesis 40550 Other Tin‐Mediated Indole Syntheses 40951 The Murphy Indole Synthesis 41252 Miscellaneous Radical‐Promoted Indole Syntheses 41453 The Graebe–Ullmann Carbazole‐Carboline Synthesis 424PART VII Cycloaddition and Electrocyclization 43554 Diels–Alder Cycloaddition 43755 Plieninger Indole Synthesis 46456 Photochemical Synthesis of Indoles and Carbazoles 46857 Dipolar Cycloaddition, Anionic, and Electrocyclization Reactions 483PART VIII Indoles from Pyrroles 49358 Electrophilic Cyclization of Pyrrole 49559 Palladium‐Catalyzed Cyclization of Pyrroles 50360 Cycloaddition Syntheses from Vinyl Pyrroles 50661 Electrocyclization of Pyrroles 51262 Indoles from Pyrrolo‐2,3‐Quinodimethanes 51763 Indoles via Dehydrogenation of Pyrroles 52064 Miscellaneous Indole Syntheses from Pyrroles 52565 Indoles via Arynes 528PART IX Indoles from Indolines 53766 Indoline Dehydrogenation 53967 Indolines to Indoles by Functionalized Elimination 55368 Indolines from Oxindoles, Isatins, and Indoxyls 558PART X Metal‐Catalyzed Indole Synthesis 57369 Copper‐Catalyzed Indole Synthesis 57570 Palladium‐Catalyzed Indole Ring Synthesis: Hegedus 58871 Palladium‐Catalyzed Indole Ring Synthesis: Mori–Ban–Heck 59272 Palladium‐Catalyzed Indole Ring Synthesis: Aryl‐Heck 59773 Palladium‐Catalyzed Indole Ring Synthesis: Oxidative Cyclization 60074 Palladium‐Catalyzed Indole Ring Synthesis: Watanabe–Cenini–Söderberg 60475 Palladium‐Catalyzed Indole Ring Synthesis: Yamanaka–Sakamoto–Sonogashira 60776 Palladium‐Catalyzed Indole Ring Synthesis: Larock 61177 Palladium‐Catalyzed Indole Ring Synthesis: Cacchi 61578 Palladium‐Catalyzed Indole Ring Synthesis: Buchwald–Hartwig 61979 Palladium‐Catalyzed Indole Ring Synthesis: Miscellaneous 62380 Rhodium‐Catalyzed Indole Ring Synthesis 63281 Gold‐Catalyzed Indole Ring Synthesis 64082 Ruthenium‐Catalyzed Indole Ring Synthesis 64583 Platinum‐Catalyzed Indole Ring Synthesis 64884 Silver‐ and Zinc‐Catalyzed Indole Ring Synthesis 65185 Iron‐, Iridium‐, and Indium‐Catalyzed Indole Ring Syntheses 65586 Nickel‐, Cobalt‐, and Molybdenum‐Catalyzed Indole Ring Syntheses 66087 Mercury‐ and Chromium‐Catalyzed Indole Ring Syntheses 66388 Miscellaneous Metal‐Catalyzed Indole Ring Syntheses 666PART XI Miscellaneous 66989 Miscellaneous Indole Ring Syntheses 671Index 676