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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概要

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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.

• 公益社団法人日本薬学会の論文
• 1975-11-25

著者

• 林 英作

  Shizuoka College of Pharmacy

• 東野 武郎

  Shizuoka College of Pharmacy

• 鈴木 清

  Shizuoka College of Pharmacy

関連論文

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