Studies on the reactions of pyrido(2,3-d)pyrimidine 3-oxide with ketones. The transformation of pyrido(2,3-d)pyrimidine 3-oxide into 1,8-naphthyridines.

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The direct reactions of pyrido[2, 3-d]pyrimidine 3-oxide (III) with ketones without a base were carried out and resulted in the transformation of III into 1, 8-naphthyridines (IV), although the yields of IV were poor. Thus, acetophenone, propiophenone, butyrophenone, and valerophenone reacted with III yielding 2-phenyl- (IV-1), 3-methyl-2-phenyl- (IV-2), 3-ethyl-2-phenyl- (IV-3), and 3-propyl-2-phenyl-1, 8-naphthyridine (IV-4), respectively, together with 2-aminonicotinaldehyde oxime (V) and 2-aminonicotinonitrile (VI). Similary acetone, 3-pentanone, 2-butanone, 2-pentanone, and 3-methyl-2-butanone resulted, respectively, in 2-methyl- (IV-5), 2-ethyl-3-methyl (IV-6), 2, 3-dimethyl- (IV-7), 3-ethyl-2-methyl (IV-8), and 2-isopropyl-1, 8-naphthyridine (IV-9) together with V and VI. Cyclopentanone, and cyclohexanone also gave 7, 8-dihydro-6H-cyclopenta[b][1, 8]naphthyridine (IV-10), and 6, 7, 8, 9-tetrahydrobenzo[b][1, 8]naphthyridine (IV-11), respectively. Moreover III and 3, 3-dimethyl-2-butanone did not lead to the expected 1, 8-naphthyridines, but gave 3, 3-dimethyl-1-(3-hydroxy-3, 4-dihydro-4-pyrido[2, 3-d]pyrimidinyl)-2-butanone (VIII). These 1, 8-naphthyridines, IV-1 to IV-12, were also prepared by the Friedlaender synthesis with 2-aminonicotinaldehyde (IX) and the corresponding ketone in the presence of sodium methoxide as a catalyst.

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