REACTION OF CROSS-CONJUGATED PUSH-PULL ENAMINO KETONES WITH 1,2-NAPHTHOQUINONE 1-METHIDES: SYNTHESIS OF 3-ARYL-1-(1H-BENZO[f]CHROMEN-2-YL)PROP-2-EN-1-ONES

Abstract

A series of 3-aryl-1-(1H-benzo[f]chromen-2-yl)prop-2-en-1-ones, both unsubstituted and containing an aryl substituent at the C-1 position was obtained via the reaction of cross-conjugated push-push enamino ketones with 2-naphthol-derived Mannich bases. The cascade process involves the hetero-Diels–Alder reaction between 1,2-naphthoquinone 1-methide formed in situ and an enaminone, followed by the elimination of a dimethylamine molecule.

Authors: Kirill S. Korzhenko, Dmitry V. Osipov, Vitaly A. Osyanin,
Pavel E. Krasnikov, Yuri N. Klimochkin