2,5-Dicarbonyl Sugars : New Intermediates for Synthesising Heterocyclic Rings. II. Synthesis of N-Substituted 5-Oxidopyridazinium Derivatives from 2,5-Diketo-D-gluconate

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概要

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• 2,5-Diketo-D-gluconate (I) (D-threo-2,5-hexodiulosonate) reacted with mono substituted hydrazines yielding anhydro 1-substituted 3-hydroxymethyl-5-hydroxypyridazinium hydroxides (IIa-g) which were a type of zwitterionic heterocyclic compounds, relatively unknown. Their structures were confirmed by their microanalytical results and spectroscopic evidences. The intermediate in the formation of anhydro 3-hydroxymethyl-5-hydroxy-1-phenyl-pyridazinium hydroxide was obtained. The structure (VIIc) (tautomeric 5-phenylhydrazone of 4-deoxy-2,5-hexodiulosonate-3-ene) could be substantiated by spectral data. The formation of IIa-g might be accounted for in terms of mono phenylhydrazone formation, enediol formation, β-hydroxycarbonyl elimination, decarboxylation and cyclization.

• 公益社団法人日本薬学会の論文
• 1974-08-25

著者

• 今田 勝美

  Research Institute, Daiichi Seiyaku Co., Ltd.

• 今田 勝美

  Research Institute Daiichi Seiyaku Co. Ltd.

関連論文

• 2,5-Dicarbonyl Sugars : New Intermediates for Synthesising Heterocyclic Rings. I. Synthesis of 4 (1H)-Pyridazinone Derivatives from Dicarbonyl Sugars
• 2,5-Dicarbonyl Sugars : New Intermediates for Synthesising Heterocyclic Rings. II. Synthesis of N-Substituted 5-Oxidopyridazinium Derivatives from 2,5-Diketo-D-gluconate

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