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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, Email: masmmail.sioc.ac.cn

L. Lu, G. Chen, S. Ma, Org. Lett., 2006, 8, 835-838.

DOI: 10.1021/ol052797a (free Supporting Information)


Abstract

An efficient synthesis of 2,3,4-trisubstituted pyrroles via intermolecular cyclization of alkylidenecyclopropyl ketones with amines was observed. A mechanism involving a distal cleavage of the C-C bond of the cyclopropane ring is discussed.

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Key Words

Pyrroles


ID: J54-Y2006-620