REACTIONS OF HYDROXYGLYCINES - NEW SYNTHETIC ROUTES TO 4-PHENYLQUINAZOLINE DERIVATIVES

Reaction of hydroxyglycine with 2-aminobenzophenones gives 1,2-dihydro-4-phenyl-quinazoline-2-carboxylic acids in high yields and under mild conditions. These can be smoothly converted into the corresponding 3,4-dihydro isomers and into quinazoline derivatives via rearrangement and oxidation by air, respectively. The X-ray crystallographic structure of 6-chloro-1,2-dihydro-1-methyl-4-phenylquinazoline-2-carboxylic acid shows the carboxylate group at C(2) and the methyl group at N(1) to be in axial positions.