Abstract
1-Phenyl-4(1H)-quinazolinones having various substituents at C-2 were synthesized and some of their reactions were examined. 1-Phenyl-2-substituted-4(1H)) quinazolinones (3) were synthesized in good yield by the reaction of 2-phenylaminobenzamide (1) with excess acid chloride under mild reaction conditions. The 2-chloroalkyl derivatives (3b-d) react with nucleophiles in a characteristic manner depending on the length of the alkyl chain. Treatment of the 2-chloromethyl derivative (3b) with nucleophiles gave 2-(substituted-methyl)-4(1H)-quinazolinones (4). Reaction of 2-chloroethyl derivative (3c) with morpholine or alcohols gave 2-(β-substituted-ethyl) derivatives (5-7) through the intermediate (8), which was identified by isolation. Allowing a chloroform solution of the 2-(γ-chloropropyl) derivative (3d) to stand afforded the 4-oxoquinazolinium salt (9a) quantitatively.
