N-isopropenylazoles: I. Direct N-isopropenylation of azoles with propyne and allene

BA Trofimov, OA Tarasova, MA Shemetova…

Index: Trofimov; Tarasova; Shemetova; Afonin; Klyba; Baikalova; Mikhaleva Russian Journal of Organic Chemistry, 2003 , vol. 39, # 3 p. 408 - 414

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Citation Number: 20

Abstract

Abstract A number of previously unknown N-isopropenyl-substituted pyrroles, indoles, and di-and-triazoles were synthesized in 20-86% yield by reaction of the corresponding azole with an equilibrium mixture of propyne with allene or pure propyne and allene in the system KOH-DMSO (105-145° C, 5-15 h, atmospheric or elevated pressure). The reaction is regioselective. The electronic and steric structure and the degree of conjugation between ...