Anionic Cyclization of (N,N-Dimethylamino)[2-(prop-2-yn-1-yloxy)aryl]acetonitriles

Tadeusz Zdrojewski; Joanna Musielak; Andrzej Jończyk

doi:10.1055/s-0028-1088061

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Anionic Cyclization of (N,N-Dimethylamino)[2-(prop-2-yn-1-yloxy)aryl]acetonitriles

Tadeusz Zdrojewski, Joanna Musielak, Andrzej Jończyk*
Warsaw University of Technology, Faculty of Chemistry, Koszykowa St. 75, 00-662 Warszawa, Poland
Fax: +48(22)6282741; e-Mail: anjon@ch.pw.edu.pl;

Abstract

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Abstract

The cyclization of (N,N-dimethylamino)[2-(prop-2-yn-1-yloxy)aryl]acetonitriles is carried out under phase-transfer conditions using powdered sodium hydroxide and benzyltriethylammonium chloride as catalyst in dimethyl sulfoxide to afford mixtures of a methylenechromane and a methylchromene via favored 6-exo-dig and 6-endo-dig processes, respectively. Several of the chromenes rearranged into benzofuranone derivatives during column chromatography on alumina and the formation of these is rationalized.

Key words

phase-transfer catalysis - carbanions - cyclizations - heterocycles - intramolecular vinylation

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