Dienaminodiones, new push-pull alkenes, from 3,4-dihydroxysalicylaldehyde-derived Schiff base

Abstract

An atom-economical one-pot synthesis of a new push-pull dienaminodiones from a 3,4-dihydroxysalicylaldehyde-derived Schiff base and indoles in the presence of phenyliodine(III) diacetate is described. Variation of indoles and anilines constitute a broad substrate scope of the methodology with good to moderate yields. Formation of Schiff base followed by an indole addition to afford dienaminodione takes place in one-pot; thus, the present method serves as a sequential multicomponent reaction. The present work also serves as a methodology to afford indole variants of natural product talaroenamine B.