Reaction of N-Aminopyridinium Derivatives. XIII. Syntheses of Pyrazolodiazines by Cyclization of N-Aminodiazinium Salts

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概要

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• N-Aminopyridazinium (IV) and N-aminopyrazinium (VI, VIII) derivatives were synthesized by N-amination of pyridazine (III) or pyrazine (V, VII) derivatives with hydroxylamine-O-sulfonic acid. By the reaction of pyrimidine derivatives (IX, XI) with hydroxylamine-O-sulfonic acid, N-aminopyrimidinium derivatives were not obtained, but pyrimidine N-oxide derivatives (X, XII) or 1-amino-4-methyl-6-oxo-1,6-dihydropyrimidine (XIV, XVI, XVII) were obtained. Therefore, N-aminopyrimidinium derivatives (XXI, XXII, XXIV, and XXVI) were synthesized by N-amination of IX and XI with O-mesitylenesulfonylhydroxylamine. Pyrazolo-diazines (XXVII-XXX, XXXV-XXXVIII) were synthesized by cycloaddition reaction of these N-aminodiazinium derivatives with acetic anhydride and sodium acetate or methyl acetylenecarboxylate. Pyrazolo [1,5-c] pyrimidine derivatives (XXXVII-XXXVIII), which are different in oriention, were obtained by 1,3-dipolar cycloaddition reaction of XXI and XXIV with methyl acetylenecarboxylate.

• 公益社団法人日本薬学会の論文
• 1974-08-25

著者

• 岡本 敏彦

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 広部 雅昭

  東京大学薬学部:文部省

• 春日 和教

  Faculty Of Pharmaceutical Sciences University Of Tokyo

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