Indole Ring Synthesis: From Natural Products to Drug Discovery

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 ring Indole 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. INDICE: 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, 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 Knölker 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 Söderberg 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

• ISBN: 978-0-470-51218-0
• Editorial: Wiley–Blackwell
• Encuadernacion: Cartoné
• Páginas: 704
• Fecha Publicación: 05/08/2016
• Nº Volúmenes: 1
• Idioma: Inglés