Indole Ring Synthesis E-Book

Gordon W. Gribble

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 815

Veröffentlichungsjahr: 2016

Beschreibung

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.

Leseprobe

Table of Contents

Cover

Title Page

About the Author

Preface

1 Introduction

1.1 Preview

1.2 Indole‐Containing Natural Products

1.3 Biological Activity of Indoles

1.4 Indole‐Containing Pharmaceuticals

1.5 Indole‐Containing Materials

1.6 Indole‐Containing Ligands

1.7 Reviews of Indole‐Ring Synthesis

References

PART I: Sigmatropic Rearrangements

2 Fischer Indole Synthesis

2.1 Preview

2.2 Methods

2.3 Applications of Fischer Indolizations

References

3 Gassman Indole Synthesis

References

4 Bartoli Indole Synthesis

References

5 Thyagarajan Indole Synthesis

References

6 Julia Indole Synthesis

References

7 Miscellaneous Sigmatropic Rearrangements

References

PART II: Nucleophilic Cyclization

8 Madelung Indole Synthesis

References

9 Wittig–Madelung Indole Synthesis

References

10 Jones–Schmid Indole Synthesis

References

11 Couture Indole Synthesis

References

12 Wender Indole Synthesis

References

13 Smith Indole Synthesis

References

14 Kihara Indole Synthesis

Reference

15 Nenitzescu 5‐Hydroxyindole Synthesis

References

16 Engler‐Kita Indole Synthesis

References

17 Bailey–Liebeskind–O’Shea Indoline–Indole Synthesis

References

18 Wright Indoline Synthesis

Reference

19 Saegusa Indole Synthesis

References

20 Ichikawa Indole Synthesis

References

21 Miscellaneous Nucleophilic Cyclizations that Form the Indole Ring

References

22 Sugasawa Indole Synthesis

References

PART III: Electrophilic Cyclization

23 Bischler Indole Synthesis

References

24 The Nordlander Indole Synthesis

References

25 Nitrene Cyclization

References

26 Cadogan–Sundberg Indole Synthesis

References

27 Sundberg Indole Synthesis

References

28 Hemetsberger Indole Synthesis

References

29 Taber Indole Synthesis

References

30 Knochel Indole Synthesis

Reference

31 Täuber Carbazole Synthesis

References

32 Quéguiner Azacarbazole Synthesis

References

33 Iwao Indole Synthesis

References

34 Hewson Indole Synthesis

Reference

35 Magnus Indole Synthesis

Reference

36 Feldman Indole Synthesis

References

37 Butin Indole Synthesis

References

38 Miscellaneous Electrophilic Cyclizations

References

PART IV: Reductive Cyclization

39 Nenitzescu

o

,β‐Dinitrostyrene Reductive Cyclization

References

40 Reissert Indole Synthesis