1H-2,3-Benzoxazin-1-ones. II. Action of Amines, Phenylhydrazine, Aluminium Chloride, and Grignard Reagents on 4-Aryl-1H-2,3-benzoxazin-1-ones

Abstract 4-Aryl-1H-2,3-benzoxazin-1-one on reaction with amines by fusion gave o-aroyl benzamides. With benzylamine in benzene they gave (2-benzylcarbamoyl)-benzophenone oximes, and with phenylhydrazine they gave 1,3-diaryl-1,2-dihydrophthalazin-4-ones. However, with anhydrous AlCl3 (12 mol) in reactive hydrocarbon substrates, they gave the corresponding o-aroylbenzophenone anils. With Grignard reagents they gave the corresponding o-aroyl-triaryl-methanols, which upon cyclization gave 1,1,4-triaryl-1(H)-2,3-benzoxazines.