Chapter 2. Synthesis of Heterocycles and Carbocycles by Electrophilic Cyclization of Alkynes

  1. Prof. Dr. François Diederich2,
  2. Prof. Dr. Peter J. Stang3 and
  3. Prof. Dr. Rik R. Tykwinski4
  1. Richard C. Larock

Published Online: 24 OCT 2005

DOI: 10.1002/3527605487.ch2

Acetylene Chemistry: Chemistry, Biology, and Material Science

Acetylene Chemistry: Chemistry, Biology, and Material Science

How to Cite

Larock, R. C. (2005) Synthesis of Heterocycles and Carbocycles by Electrophilic Cyclization of Alkynes, in Acetylene Chemistry: Chemistry, Biology, and Material Science (eds F. Diederich, P. J. Stang and R. R. Tykwinski), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527605487.ch2

Editor Information

  1. 2

    Laboratorium für Organische Chemie, ETH Hönggerberg, HCI, CH-8093 Zürich, Switzerland

  2. 3

    Department of Chemistry, University of Utah, 315S 1400E, Rm. 2020, 84112 Salt Lake City, USA

  3. 4

    Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada

Author Information

  1. Department of Chemistry, 1605 Gilman Hall, Iowa State University, Ames, IA 50011-3111, USA

Publication History

  1. Published Online: 24 OCT 2005
  2. Published Print: 14 DEC 2004

ISBN Information

Print ISBN: 9783527307814

Online ISBN: 9783527605484

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Keywords:

  • acetylene chemistry;
  • biology and material science;
  • electrophilic cyclization of alkynes;
  • heterocycles;
  • carbocycles;
  • cyclization of oxygen compounds;
  • cyclization of sulfur compounds;
  • cyclization of selenium compounds;
  • cyclization of nitrogen compounds;
  • cyclization of carbon onto acetylenes;
  • experimental procedures

Summary

This chapter contains sections titled:

  • Introduction

  • Cyclization of Oxygen Compounds

    • Cyclization of Acetylenic Alcohols

    • Cyclization of Acetylenic Phenols

    • Cyclization of Acetylenic Ethers

    • Cyclization of Acetylenic Acids and Derivatives

    • Cyclization of Acetylenic Aldehydes and Ketones

  • Cyclization of Sulfur and Selenium Compounds

  • Cyclization of Nitrogen Compounds

    • Cyclization of Acetylenic Amines

    • Cyclization of Acetylenic Amides

    • Cyclization of Acetylenic Carbamates

    • Cyclization of Acetylenic Sulfonamides

    • Cyclization of Acetylenic Enamines and Imines

    • Cyclization of Other Acetylenic Nitrogen Functional Groups

  • Cyclization of Carbon onto Acetylenes

    • Cyclization of Acetylenic Carbonyl Compounds and Derivatives

    • Cyclization of Diacetylenes

    • Cyclization of Aryl Acetylenes

    • Cyclization of Acetylenic Organometallics

  • Conclusions

  • Representative Experimental Procedures

    • Synthesis of α-Methylene-γ-butyrolactones by Carbonylation of 1-Alkyn-4-ols

    • Synthesis of 1-Alkoxyisochromenes by Cyclization of 2-(1-Alkynyl)benzaldehydes

    • Synthesis of 3-Aryl(vinylic)indoles by Palladium-catalyzed Cross-coupling of Aryl Halides or Vinylic Triflates and 2-(1-Alkynyl)trifluoroacetanilides

    • Synthesis of Pyridines by the Gold-catalyzed Cross-coupling of Ketones and Propargyl Amine

    • Synthesis of 4-Iodoisoquinolines by the Cyclization of Iminoalkynes

    • Synthesis of Cyclic Amines by Acetylene-Iminium Ion Cyclizations

  • Acknowledgements