Indole ring synthesis: from natural products to drug discovery

Content: 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 Tauber Carbazole Synthesis 301    32 Queguiner 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,     Dinitrostyrene Reductive Cyclization 325    40 Reissert Indole Synthesis 332    41 Leimgruber   Batcho Indole Synthesis 338    42 Pschorr   Hoppe Indole Synthesis 349    43 M  kosza 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 Knolker Carbazole Synthesis 391    48 Miscellaneous Oxidative Cyclizations 396    PART VI Radical Cyclization 403    49 Fukuyama Indole Synthesis 405    50 Other Tin   Mediated Indole Syntheses 409    51 The Murphy Indole Synthesis 412    52 Miscellaneous Radical   Promoted Indole Syntheses 414    53 The Graebe   Ullmann Carbazole   Carboline Synthesis 424    PART VII Cycloaddition and Electrocyclization 435    54 Diels   Alder Cycloaddition 437    55 Plieninger Indole Synthesis 464    56 Photochemical Synthesis of Indoles and Carbazoles 468    57 Dipolar Cycloaddition, Anionic, and Electrocyclization Reactions 483    PART VIII Indoles from Pyrroles 493    58 Electrophilic Cyclization of Pyrrole 495    59 Palladium   Catalyzed Cyclization of Pyrroles 503    60 Cycloaddition Syntheses from Vinyl Pyrroles 506    61 Electrocyclization of Pyrroles 512    62 Indoles from Pyrrolo   2,3   Quinodimethanes 517    63 Indoles via Dehydrogenation of Pyrroles 520    64 Miscellaneous Indole Syntheses from Pyrroles 525    65 Indoles via Arynes 528    PART IX Indoles from Indolines 537    66 Indoline Dehydrogenation 539    67 Indolines to Indoles by Functionalized Elimination 553    68 Indolines from Oxindoles, Isatins, and Indoxyls 558    PART X Metal   Catalyzed Indole Synthesis 573    69 Copper   Catalyzed Indole Synthesis 575    70 Palladium   Catalyzed Indole Ring Synthesis: Hegedus 588    71 Palladium   Catalyzed Indole Ring Synthesis: Mori   Ban   Heck 592    72 Palladium   Catalyzed Indole Ring Synthesis: Aryl   Heck 597    73 Palladium   Catalyzed Indole Ring Synthesis: Oxidative Cyclization 600    74 Palladium   Catalyzed Indole Ring Synthesis: Watanabe   Cenini   Soderberg 604    75 Palladium   Catalyzed Indole Ring Synthesis: Yamanaka   Sakamoto   Sonogashira 607    76 Palladium   Catalyzed Indole Ring Synthesis: Larock 611    77 Palladium   Catalyzed Indole Ring Synthesis: Cacchi 615    78 Palladium   Catalyzed Indole Ring Synthesis: Buchwald   Hartwig 619    79 Palladium   Catalyzed Indole Ring Synthesis: Miscellaneous 623    80 Rhodium   Catalyzed Indole Ring Synthesis 632    81 Gold   Catalyzed Indole Ring Synthesis 640    82 Ruthenium   Catalyzed Indole Ring Synthesis 645    83 Platinum   Catalyzed Indole Ring Synthesis 648    84 Silver    and Zinc   Catalyzed Indole Ring Synthesis 651    85 Iron   , Iridium   , and Indium   Catalyzed Indole Ring Syntheses 655    86 Nickel   , Cobalt   , and Molybdenum   Catalyzed Indole Ring Syntheses 660    87 Mercury    and Chromium   Catalyzed Indole Ring Syntheses 663    88 Miscellaneous Metal   Catalyzed Indole Ring Syntheses 666    PART XI Miscellaneous 669    89 Miscellaneous Indole Ring Syntheses 671    Index 676