Preparation and Reactions of Quinazoline Reissert Compound (3-Benzoyl-3, 4-dihydro-4-quinazolinecarbonitrile)

抄録

The benzoylation of 3, 4-dihydro-4-quinazolinecarbonitrile (3) with benzoyl chloride in pyridine gave quinazoline Reissert compound (1, 3-benzoyl-3, 4-dihydro-4-quinazolinecarbonitrile) in 82% yield. The alkaline hydrolysis of 1 in methanol resulted in the formation of quinazoline (2) and benzoic acid (4). Acid hydrolysis gave 2-benzamido-2-(2-aminophenyl) acetonitrile (6), 4, and 2. The HCl salt of 1 existed predominantly in the cyclic amidinium structure of the type 8. Compound 1 reacted with sodium hydride in dimethylformamide to yield 4-quinazolinecarbonitrile (9), α-phenyl-4-quinazolinylmethyl benzoate (10), and O-benzoylbenzoin (11). In the present paper we compare the chemical properties of 1 with those of isoquinoline Reissert compound (13, 2-benzoyl-1, 2-dihydro-1-isoquinolinecarbonitrile).