Cyclization Reactions of Some 5-Nitro- and 5-Nitroso-6-benzylidenehydrazinouracils

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概要

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• The treatment of 6-(benzylidene-1'-methylhydrazino)-3-methyl-5-nitrouracil (I) with sulfuric acid in acetic acid gave a mixture of 1,6-dimethyl-5,7-dioxo-8-nitro-3-phenyl-1,5,6,7-tetrahydro-s-triazolo [4,3-c] pyrimidine (III) and 1,5-dimethyl-3-phenylpyrazolo-[3,4-d] pyrimidine-4,6 (5H, 7H) dione. The reaction in the presence of potassium nitrate under the same conditions gave exclusively III. The reaction of 6-(benzylidene-1'-methylhydrazino)-3-methyluracil with potassium nitrate in acetic acid in the presence of sulfuric acid gave a mixture of 3-phenyltoxoflavin and 3-phenyl-1-demethyltoxoflavin. The treatment of 6-benzylidenehydrazino-3-methyl-5-nitrouracil with potassium nitrate in acetic acid (with or without sulfuric acid) gave 5,7-dioxo-6-methyl-8-nitro-3-phenyl-1,5,6,7-tetrahydro-s-triazolo [4,3-c] pyrimidine. The treatment of 6-benzylidenehydrazino-3-methyluracil with sodium nitrite in acetic acid at low temperature gave the corresponding 5-nitroso derivative, which was converted into 3,6-dimethyl-2,4,5,7 (1H, 3H, 6H, 8H)-pyrimido [5,4-g] pteridinetetrone by treatment with a mixture of acetic acid and sulfuric acid.

• 公益社団法人日本薬学会の論文
• 1975-08-25

著者

• 米田 文郎

  Faculty Of Pharmaceutical Sciences Kyoto University

• 永松 朝文

  Faculty Of Pharmaceutical Sciences Okayama University

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