SYNTHESIS AND REACTION OF 2-(ALPHA-NAPHTHYL)-4-(3H)-QUINAZOLINONE

Reaction of 2-(alpha-naphthy)-3,1-(4H) benzoxazin-4-one with formamide in dry xylene gave 2-(alpha-naphthyl)-4- (3H)-quinazolinone (1). Compound (1) reacteed with methyl iodide, POCl3/PCl5, ethyl chloroacetate or dimethyl sulphate to give 3-methyl-, 4-chloro-, 4-carbinol- and 4-methyoxy quinazolinone derivatives, (2), (6) and (8 a,b), respectively. The condensation of (2), with benzaldehyde or p-anisaldehyde gave 3-styryl and 3-(p-methoxy stryl)-quinozolinone derivatives (3 a,b). Fusion of (2) with phthalimide or succinic anhydride gave the corresponding phthalimido and succinimdo derivatives (4) and (5), respectively. The reaction of (6) with aniline, hydrazine hydrate and sodium azide yielded the corresponding 4-(anilino, hydrazino and azido)-quinazolinone derivatives (7 a-c), respectively. Treatment of (8 a) with hydrazine hydrate, phenyl hydrazine, aniline and p-toludidine gave the corresponding amide derivatives (9 a-d) respectively.