The Journal of organic chemistry

General and regioselective synthesis of substituted pyrroles by Metal-Catalyzed or spontaneous cycloisomerization of (Z)-(2-En-4-ynyl) amines

B Gabriele, G Salerno, A Fazio

Index: Gabriele, Bartolo; Salerno, Giuseppe; Fazio, Alessia Journal of Organic Chemistry, 2003 , vol. 68, # 20 p. 7853 - 7861

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Citation Number: 112

Abstract

A general and regioselective synthesis of substituted pyrroles 2 by cycloisomerization of readily available (Z)-(2-en-4-ynyl) amines 1 is reported. Spontaneous cycloisomerization leading to 2 occurred in the course of preparation of enynamines bearing a terminal triple bond or a triple bond substituted with a phenyl or a CH2OTHP group. When the triple bond was substituted with an alkyl or alkenyl group, enynamines were stable and could be ...