Tetrahedron Letters

[3+ 2] Cycloadditions of α-acyl ketene dithioacetals with propargylamines: pyrrole synthesis in water

CQ Ren, CH Di, YL Zhao, JP Zhang

Index: Ren, Chuan-Qing; Di, Chong-Hui; Zhao, Yu-Long; Zhang, Jing-Ping Tetrahedron Letters, 2013 , vol. 54, # 11 p. 1478 - 1481

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Citation Number: 9

Abstract

A series of 2, 3, 4-trisubstituted and 1, 2, 3, 4-tetrasubstituted pyrroles were synthesized via [3+ 2] cycloaddition of α-acyl ketene dithioacetals (or related substrates) with commercially available propargylamines as 1, 3-dipoles in water. Most of the reactions can be performed in the absence of an external base. The reaction of secondary amine (N-methylprop-2-yn-1- amine) with α-acyl ketene dithioacetals showed different reaction behaviours depending ...