Studies on the Reaction of Quinazoline 3-Oxide with Ketone. The Transformation of Quinazoline 3-Oxide into Quinoline Derivatives

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The direct reaction of quinazoline 3-oxide (I) with ketones (III) without a base was carried and resulted in the transformation of I into quinoline derivatives (II), although the yields of II were very poor (small percentage) in some cases. Thus, the reaction of I with acetophenone gave 2-phenylquinoline (II-3), quinazoline (IV) and 4, 4'-biquinazoline (V), with propiophenone, 3-methyl-2-phenylquinoline (II-4) and V, with acetone, 2-methylquinoline (II-5), IV, V, and 2-aminobenzaldoxime (VI), with 3-pentanone, 2-ethyl-3-methylquinoline (II-6), IV and VI, with 2-butanone, 2, 3-dimethylquinoline (II-7) and IV, with 2-pentanone, 3-ethyl-2-methylquinoline (II-8), IV and VI, with 3-methyl-2-butanone, 2-isopropylquinoline (II-9), IV and 4-methylquinazoline 3-oxide (VII), with 3, 3-dimethyl-2-butanone, 2-tert-butylquinoline (II-10), IV, V, and VII, with 4-methyl-2-pentanone, 2-isobutylquinoline (II-11), IV and V, with cyclopentanone, 2, 3-dihydro-1H-cyclopenta [b] quinoline (II-12), with cyclohexanone, 1, 2, 3, 4-tetrahydroacridine (II-13), respectively.