Acetate-Promoted Aldol-Type Reaction: Scope and Reactivity of Acetates and Aldehydes

Abstract

Potential of acetates and related compounds in glacial acetic acid as a catalyst for aldol-type condensation reactions was examined. Reactions of cycloalkanones or selected heteroaromatics with aldehydes in presence of 10 mol% of various acetates in acetic acid afforded α,α'-bis(substituted-benzylidene)cycloalkanones and substituted-benzylidene-mackinazolinones, respectively, in good yields. Among the compounds tested, ammonium acetate is the best and effective especially towards the reactions of mackinazolinone and aliphatic aldehydes to afford 6-alkylidenemackinazolinones.