Tetrahedron

Ambivalent role of metal chlorides in ring opening reactions of 2H-azirines: synthesis of imidazoles, pyrroles and pyrrolinones

S Auricchio, AM Truscello, M Lauria, SV Meille

Index: Auricchio, Sergio; Truscello, Ada M.; Lauria, Mirvana; Meille, Stefano V. Tetrahedron, 2012 , vol. 68, # 36 p. 7441 - 7449

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Citation Number: 14

Abstract

2H-Azirines were found to react with imines, enaminones and enaminoesters in the presence of metal salts. Imidazoles, pyrroles and new pyrrolinones derivatives are isolated in good overall yields. The role of metal salts was investigated as they can act as Lewis acids or electron donors. Mechanisms are proposed suggesting that imidazoles arise from addition of azirine to imines via radical or ionic mechanism; pyrroles and pyrrolinones are ...