1,3-Dipolar Cycloaddition Reactions of Thiazolo[5,4-d]pyrimidine 1-0xides with Acetylenic Esters Involving New Ring Transformations of the Thiazole Nucleus(Organic,Chemical)

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概要

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• The reaction of 2-(methoxycarbonyl)-4.6-dimethylthiazolo[5,4-d]pyrimidine-5,7(4H,6H)-dione 1-oxide (1) with dimethyl acetyienedicarboxylate resulted in a new ring transformation of the thiazole nucleus to give 5-[2-methoxalyl-1.2-bis(methoxycarbonyl)vinyl]imino-1,3-dimethyl-6-thiobarbituric acid (4), 6,7-bis(methoxycarbonyl)-1,3-dimethylpyrimido[4,5-b][1,4]thiazine-2,4-(1H,3H)-dione (8), 6,7-bis(methoxycarbonyl)-1,3-dimethylpyrrolo[3,2-d]pyrimidine-2,4(1H,3H)-dione (9), and anhydro-2-[1-methoxalyl-1-(O-sodiummethoxycarbonyl)]methyl-4,6-dimethyi-thiazolo[5,4-d]pyrimidine-5,7(4H,6H)-dione hydroxide (11). Analogously, the reaction of 1 with ethyl phenylpropiolate gave 5-[2-benzoyl-2-(ethoxycarbonyl)-1-(methoxycarbonyl)vinyl]imino-1.3-dimethyl-6-thiobarbituric acid (22), 5-benzoyl-7-(ethoxycarbonyl)-6-(methoxycarbonyl)-1,3-dimethylpyrimido[4,5-b][1,4]thiazine-2,4(1H,3H)-dione (23), and 7-(ethoxycarbonyl)-6-(methoxycarbonyl)-1,3-dimethylpyrrolo[3,2-d]pyrimidine-2.4(1H,3H)-dione (24). The structures of these products were supported by their spectral [iufrared (IR), mass (MS), ultraviolet (UV), proton nuclear magnetic resonance (^1H-NMR) or carbon-13 nuclear magnetic resonauce (^<13>C-NMR)] data or by single-crystal X-ray diffraction analysis as well as by chemical transformations. The ring transformation of the thiazole nucleus can be best explained by taking into account the initial involvement of a 1,3-dipolar cycloaddition reaction.

• 社団法人日本薬学会の論文
• 1987-01-25

著者

• 河合 賢一

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 乙益 寛隆

  Hoshi College of Pharmacy

• 河合 賢一

  Faculty Of Pharmaceutical Sciences Hoshi University

• 金沢 一

  Pharmaceutical Institute, School of Medicine, Keio, University

• 市場 みすず

  Pharmaceutical Institute, School of Medicine, Keio, University

• 田村 善蔵

  Pharmaceutical Institute, School of Medicine, Keio, University

• 千賀 慶太郎

  Pharmaceutical Institute, School of Medicine, Keio, University

• 乙益 寛隆

  Faculty of Pharmaceutical Sciences, Hoshi University

• 千賀 慶太郎

  Pharmaceutical Institute School Of Medicine Keio University

• 千賀 慶太郎

  慶応大 病院

• 千賀 慶太郎

  慶応義塾大学病院薬剤部

• 乙益 寛隆

  Faculty Of Pharmaceutical Sciences Hoshi University

• 田村 善藏

  慶應義塾大学病院薬剤部

• 金沢 一

  慶應義塾大学病院薬剤部

• 田村 善蔵

  Pharmaceutical Institute School Of Medicine Keio University

• 市場 みすず

  Pharmaceutical Institute School Of Medicine Keio University

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