Tetrahedron

Orthogonal synthesis of pyrroles and 1, 2, 3-triazoles from vinyl azides and 1, 3-dicarbonyl compounds

EPJ Ng, YF Wang, BWQ Hui, G Lapointe, S Chiba

Index: Ng, Eileen Pei Jian; Wang, Yi-Feng; Hui, Benjamin Wei-Qiang; Lapointe, Guillaume; Chiba, Shunsuke Tetrahedron, 2011 , vol. 67, # 40 p. 7728 - 7737

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Citation Number: 43

Abstract

Tri-and tetrasubstituted N–H pyrroles were prepared by the simple treatment of vinyl azides with 1, 3-dicarbonyl compounds in toluene at 100° C via 2H-azirine intermediates generated in situ. When the reactions of vinyl azides and 1, 3-dicarbonyl compounds were performed in DMF in the presence of a catalytic amount of K2CO3, 1-vinyl-1, 2, 3-triazoles were obtained via 1, 3-dipolar cycloaddition. These methodologies exploited orthogonal modes of ...