Ring-Opening Cyclization of Alkylidenecyclopropyl Ketones with Amines. An Efficient Synthesis of 2,3,4-Trisubstituted Pyrroles

Lianghua Lu,† Guofei Chen,‡ and Shengming Ma*†‡
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China, and Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
Org. Lett., 2006, 8 (5), pp 835–838
DOI: 10.1021/ol052797a
Publication Date (Web): February 9, 2006
Copyright © 2006 American Chemical Society
†

 Chinese Academy of Sciences.

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‡

 Zhejiang University.

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*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, masm@mail.sioc.ac.cn

Abstract

Abstract Image

An efficient synthesis of 2,3,4-trisubstituted pyrroles via intermolecular cyclization of alkylidenecyclopropyl ketones with amines was observed. The addition of anhydrous MgSO4 improved the yields of the products 3. A possible mechanism involving the distal cleavage of the C−C bond of cyclopropane ring was proposed.

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History

  • Published In Issue March 02, 2006
  • Received November 18, 2005

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