Direct preparation of benzofurans from O-arylhydroxylamines.

Contiero, Fanny and Jones, Kevin M. and Matts, Edward A. and Porzelle, Achim and Tomkinson, Nicholas C. O. (2009) Direct preparation of benzofurans from O-arylhydroxylamines. Synlett (18). pp. 3003-3006. ISSN 0936-5214

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Abstract

Reaction of O-arylhydroxylamine hydrochlorides with either cyclic or acyclic ketones in the presence of methanesulfonic acid leads directly to the benzofuran deriv. via a proposed one-pot condensation-rearrangement-cyclization reaction sequence in good to excellent yields. E.g., in the presence of methanesulfonic acid, reaction of H2NOPh.HCl and cyclohexanone gave 70% benzofuran deriv. I.