Synthesis of new 4(3H)-quinazolinone derivatives under solvent-free conditions using PEG-400

Abstract

Anthranilic acid 1 was reacted with chloroacetyl chloride in dichloromethane containing triethylamine to yield 2-chloromethyl benzo[d][1,3]oxazin-4-one 2, which on treatment with aromatic amines yielded 2-(chloromethyl)-3-arylquinazolin-4(3H)-one 3. The latter on reaction with nitrogen nucleophiles such as ethyl piperidine-4-carboxylate, morpholine and piperidine-4-one in CH3CN containing K2CO3 and catalytic amount of KI under refluxing conditions, gave 1-(4-oxo-3-aryl-3,4- dihydroquinazolin-2-ylmethyl)piperidine-4-carboxylic acid ethyl ester (4), 2-morpholine-4-ylmethyl-3-aryl-3H-quinazolin-4-one (5), 2-(4-oxopiperidine-1- ylmethyl)-3-aryl-3H-quinazolin-4-one (6) respectively. All the above reactions have been carried out under solvent-free conditions in the presence of PEG-400 by simple physical grinding in a mortar and pestle. The structures of all the new products obtained in the present work are supported by spectral and analytical data (IR, 1H NMR and Mass spectroscopy). ©ARKAT USA, Inc.