Synthesis of O-alkyl derivatives of dehydrozingerone analogues

Abstract

Vanillin and isobuthyl methyl ketone (4-methylpentan-2-one) reacts under Claisen-Schmidt conditions yielding corresponding dehydrozingerone analogue, (E)-1- (4-hydroxy-3-methoxyphenyl)-5-methylhex-1-en-3-one. A small series of its O-alkyl derivatives was prepared by alkylation of free phenolic group with corresponding alkyl halides. Products had been tested for their biological activity and demonstrated relatively strong in vitro antimicrobial activity towards different strains of bacteria and fungi. All new compounds were well characterized by IR, 1H and 13C NMR spectroscopy and physical dat.

Keywords

• vanillin
• dehydrozingerone
• enone system
• microbiological activity