Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

Abstract

N-Benzylation of acylhydrazones of the hydroxybenzaldehyde series with 3,5-di-tert-butyl-4-hydroxybenzyl acetate was performed at room temperature in the absence of acid or base catalysts. Carboxamides do not react with 3,5-di-tert-butyl-4-hydroxybenzyl acetate under similar conditions. N-Benzylation of isoniazid and (diphenylphosphoryl)acetic acid hydrazones was shown to be an efficient method for the synthesis of new hybrid compounds containing moieties of biologically active acylhydrazones and sterically hindered phenols. N-Benzyl derivatives of isoniazid and (diphenylphosphoryl)acetic acid hydrazones containing a hydroxy group at the ortho position of the aromatic ring are formed as individual E isomers with respect to the C-N double bond.