NEW ASPECTS OF THE 1,3-DIPOLAR CYCLOADDITION OF THIAZOLIUM N-IMINES WITH DIMETHYL ACETYLENEDICARBOXYLATE (DMAD)
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概要
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The reaction of thiazolium N-imines with DMAD in methanol was studied. 4-Methylthiazolium N-imine (1a) reacted with DMAD to give three products, dimethyl [2-(3', 4'-bismethoxycarbonyl-1-pyrazolyl)-propenylthio] fumarate (4,1 : 2 adduct)^<1b)>, dimethyl 2,3-bis [2'-(3", 4"-bismethoxycarbonyl-1"-pyrazolyl)-propenylthio] succinate (5,2 : 3 adduct), and 3-methyl-6-methoxycarbonyl-8-oxidothiazolo [3,2-b] pyridazinium (6a). The structure of 6a was established by X-ray analysis and infrared (IR) spectral data. In a similar reaction with 4,5-dimethylthiazolium N-imine (1b), 2,3-dimethyl-6,7-bismethoxycarbonyl-7,7a-dihydro-4H-thiazolo [3,2-b] pyrazole (2'b, 1 : 1 adduct) was isolated, and this compound, when heated in ethanol, underwent ring expansion to be converted into an 8-oxidothiazolo [3,2-b] pyridazinium derivative (6b), an analog of 6a.
- 社団法人日本薬学会の論文
- 1984-06-25
著者
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土井 光暢
大阪薬大
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石田 寿昌
大阪薬大
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石田 寿昌
Osaka University of Pharmaceutical Sciences
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井上 正敏
Osaka University of Pharmaceutical Sciences
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井上 正敏
大阪薬大
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土井 光暢
Osaka University of Pharmaceutical Sciences
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平野 弘
Osaka College of Pharmacy
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杉山 和明
Osaka College of Pharmacy
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山下 まゆみ
Osaka College of Pharmacy
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石田 寿晶
大阪薬科大学
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Doi Mitsunobu
Department Of Physical Chemistry Osaka University Of Pharmaceutical Sciences
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井上 正敏
Department Of Physical Chemistry Osaka University Of Pharmaceutical Sciences
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