Competitive Reaction of -OH and -NH2 Functional Groups on Synthesis of Bioactive ortho-Cetamol Derivative (4-Allyl-2-methoxy-N-acetyl-o-amino phenol) from Amino-Eugenol

摘要

The main aim of this research was to develop new or novel compounds with potential biological activity from readily accessed natural products, in particular eugenol (1). A new ortho-cetamol derivative (4-allyl-2-methoxy-N-acetyl-o-amino phenol) was synthesized from amino-eugenol which was prepared by series reactions from eugenol (4-allyI-2-methoxy-phenol). Eugenol has been transformed to its nitro eugenol (2) in good yield by adding potassium hydrogen sulfate and ammonium nitrate. The nitro group of eugenol reduced smoothly to amino-eugenol (3) by treating with zinc and formic acid. Reaction of amino eugenol with acetyl chloride in the presence of sodium carbonate produced 2-acetato-5-allyl-3-methoxy-aniline (4) (16.16 %) and 4-allyl-2-methoxy-N-acetyl-o-aminophenol (5) (58.58 %) and competitive reaction occured between -OH and -NH2 groups of amino-eugenol during the acylation reaction due to steric hindrance.