Pyrimidine Derivatives. XI. Facile Carbon-Carbon Bond-Cleavage Reaction of 6-Bromomethylpyrimidinediones and (2,4-Dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)methyl Nitrate via 6-Formyl Derivatives

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概要

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• The reaction of 5-bromo-6-bromomethyl-1,3-dimethyl- (1a) and 5-bromo-6-bromomethyl-1-(3-bromopropyl)-3-methyl-2,4(1H, 3H)-pyrimidinedione (4a) with 1.0 and 2.0 eq of the sodium salt of 2-nitropropane yielded a mixture of 6-formyl (2 and 5a) and carbon-carbon bond-cleavage products (3 and 6a). When a large excess of the sodium salt of 2-nitropropane was used, 3 and 6a were obtained as sole products, respectively. The nitrates [(5-bromo-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)methyl nitrate (1b) and the dinitrate of 5-bromo-6-hydroxymethyl-1-(3-hydroxypropyl)-3-methyl-2,4(1H, 3H)-pyrimidinedione (4b)] were exclusively converted to 6-formylpyrimidines (2 and 5b) or 6-unsubstituted pyrimidinediones (3 and 6b) by reaction with 1.0 or 2.0 eq of sodium methoxide, respectively. The dinitrate of 5-bromo-1-(2-hydroxyethyl)-6-hydroxymethyl-3-methyl-2,4(1H, 3H)-pyrimidinediones (7) was treated with sodium methoxide to yield 2-(5-bromo-6-formyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)ethyl nitrate (8), a 3,4-dihydropyrimido[6,1-c][1,4]oxazine derivative (9) and 2-(5-bromo-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)ethyl nitrate (10). A plausible reaction mechanism is presented.

• 公益社団法人日本薬学会の論文
• 1993-12-15

著者

• 木下 敏夫

  School of Pharmaceutical Sciences, Nagasaki University

• 谷元 陽子

  School of Pharmaceutical Sciences, Nagasaki University

• 木下 敏夫

  School Of Pharmaceutical Sciences Nagasaki University

• 大石 浩志

  School Of Pharmaceutical Sciences Nagasaki University

• 谷元 陽子

  School Of Pharmaceutical Sciences Nagasaki University

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