Tetrahedron

Acid-promoted rearrangement of arylmethyl azides: applications toward the synthesis of N-arylmethyl arenes and polycyclic heteroaromatic compounds

J Tummatorn, C Thongsornkleeb, S Ruchirawat

Index: Tummatorn, Jumreang; Thongsornkleeb, Charnsak; Ruchirawat, Somsak Tetrahedron, 2012 , vol. 68, # 24 p. 4732 - 4739

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Citation Number: 20

Abstract

An acid-promoted Aubé–Schmidt's rearrangement of arylmethyl azides provides a useful in situ iminium ion intermediate, which can be efficiently trapped by various nucleophiles. We report here the reaction of this iminium ion with aromatic nucleophiles to give N-arylmethyl arenes and the reaction with heteroaromatic compounds to give fused polycyclic heteroaromatic products in a formal [4+ 2] cycloaddition. The short synthesis of ...