抄録
In order to examine the reactivity of ring carbon at 4-position towards nucleophilic reagents, reaction of 4-methoxyquinazoline (III), 2-methyl-2-(4-quinalinyl) propiophenone (IV), and α-phenyl-4-quinalineacetonitrile (V) with various nucleophilic reagents was carried out. The reaction of III with phenylacetonitrile, ethyl cyanoacetate, and malononitrile in methanol, in the presence of a methoxide ion, respectively afforded the corresponding V, methyl α-cyano-4-quinazolineacetate (VI), and 4-quinazolinemalononitrile (VII). The reaction of IV with methoxide ion, aniline, butylamine, piperidine, and hydrazine respectively afforded the corresponding III, 4-anilino- (X), 4-butylamino- (XI), 4-piperidino- (XII), and 4-hydrazino-quinazoline (XIII). In the reaction of IV with acetone and acetophenone, in the presence of sodium amide, β-diketones corresponding to 4-isopropylquinazoline (XV) were produced as 1-phenyl-1, 3-butanedione (XVI) and 1, 3-diphenyl-1, 3-propanedione (XVII). The reaction of V with methoxide ion, aniline, butylamine, and piperidine respectively afforded III, X, XI, and XII.
