Synthesis and Reactions of 2,3-Dihydrothiazolo[3,2-α]pyrimidine Derivatives(Organic,Chemical)

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概要

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• The reaction of 2-amino-2-thiazoline (1) with acetylene carboxylates (2) afforded 5-substituted 2,3-dihydro-7H-thiazolo[3,2-α]pyrimidin-7-ones (3). 7-Bromomethyl-2, 3-dihydro-5H-thiazolo-[3,2-α]pyrimidin-5-one (10) was obtained by the reaction of 1 with γ-bromoacetoacetyl bromide. Treatment of 10 with N-bromosuccinimide provided the 6-bromo compound (12). The 7-bromomethyl compounds (10 and 12) were converted to 7-morpholinomethyl derivatives by treatment with morpholine. When 3a (unsubstituted-), 3b (5-ethoxycarbonyl-), and 3c (5-hydroxymethyl-) were treated with 5% hydrochloric acid, covalent hydration occurred across the 5,6-carbon-carbon bond, giving 5-hydroxy-2,3,5,6-tetrahydro-7H-thiazolo[3,2-α]pyrimidin-7-one derivatives (16a, 16b, and 16c). On the other hand, in the case of 11 (7-methyl-) and 17 (5-phenyl-), the dihydrotbiazole ring was cleaved to give 3(and 1)-(2-mercaptoethyl)-6-methyl(and phenyl)-2,4(1H,3H)-pyrimidinedione (19 and 18).

• 公益社団法人日本薬学会の論文
• 1987-01-25

著者

• 木下 敏夫

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 古川 淳

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 古川 淳

  School Of Pharmaceutical Sciences Nagasaki University

• 木下 敏夫

  School of Pharmaceutical Sciences, Nagasaki University

• 上島 泰二

  Faculty Of Pharmaceutical Sciences Nagasaki University

• 斉藤 孝二

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 吉田 泰史

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 吉田 泰史

  Faculty Of Pharmaceutical Sciences Nagasaki University

• 木下 敏夫

  School Of Pharmaceutical Sciences Nagasaki University

• 斉藤 孝二

  Faculty Of Pharmaceutical Sciences Nagasaki University

関連論文

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