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

Author:
Tummatorn, Jumreang, Thongsornkleeb, Charnsak, Ruchirawat, Somsak
Source:
Tetrahedron 2012 v.68 no.24 pp. 4732-4739
ISSN:
0040-4020
Subject:
antimalarials, aromatic hydrocarbons, azides, chemical reactions, chemical structure, heterocyclic compounds
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 isocrytolepine, an antimalarial agent, further demonstrated the utility of this process.
Agid:
1094993