Gordon W. Gribble

Indole Ring Synthesis (eBook, ePUB)

From Natural Products to Drug Discovery

• Format: ePub

Produktbeschreibung

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.

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Produktdetails

• Verlag: John Wiley & Sons
• Seitenzahl: 704
• Erscheinungstermin: 6. Juni 2016
• Englisch
• ISBN-13: 9781118683859
• Artikelnr.: 45252727

Autorenporträt

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.

Inhaltsangabe

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