A novel facile synthesis of 2, 5-di-and 2, 3, 5-trisubstituted pyrroles

…, NA Kalinina, LM Sinegovskaya, J Henkelmann

Index: Trofimov; Tarasova; Mikhaleva; Kalinina; Sinegovskaya; Henkelmann Synthesis, 2000 , # 11 p. 1585 - 1590

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Citation Number: 36

Abstract

Abstract: Heterocyclization of ketoximes with propyne or allene in superbase systems MOR/DMSO (M= K, Cs; R= H, t-Bu), which leads to 2-alkyl (aryl, hetaryl)-5-methyl-and 2, 3- dialkyl-5-methylpyrroles or 2-methyl-4, 5, 6, 7-tetrahydroindole in yields of up to 63%, has been accomplished for the first time. The reaction is mostly regioselective affording mainly or exclusively 2, 5-di-and 2, 3, 5-trisubstituted pyrroles. The minor isomers in most cases are ...