Indole Ring Synthesis

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 En...

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 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.

Inhalt
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…

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