Syntheses of Pyrimido [4,5-c] pyridazine Derivatives. II. A Novel Reaction of α-Diazo-β-oxo-5-(4-chloropyrimidine) propionate with Triphenyl Phosphine leading to 1,4-Dihydro-4-oxopyrimido-[4,5-c] pyridazine-3-carboxylate
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概要
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A new and convenient synthetic method was presented for the derivatives of the pyrimido [4,5-c] pyridazine. Reactions of α-diazo-β-oxo-5-(4-chloro-2-substituted pyrimidine) propionates (1a-c) with triphenyl phosphine afforded ethyl 1,4-dihydro-4-oxo-7-substituted pyrimido [4,5-c] pyridazine-3-carboxylates (3a-c) in good yields. α-Diazo-β-oxo-5-(4-methoxy-2-methylthiopyrimidine) propionate (5a), when treated with triphenyl phosphine in the same conditions, yielded {[1-ethoxycarbonyl-2-oxo-2-(4-methoxy-2-methylthio-5-pyrimidinyl) ethylidene] hydrazono} triphenyl phosphorane (6a) which was an intermediate for the 7-methylthio derivative (3a). The conversion of 6a into 3a was effected by treating with aqueous alcohol via ethyl α-hydrazono-β-oxo-5-(4-methoxy-2-methylthiopyrimidine) propionate (7a). The 2-phenyl derivative (5b) gave the 7-phenyl analog (3b). Reaction mechanisms for 1 leading to 3 were discussed.
- 公益社団法人日本薬学会の論文
- 1978-01-25
著者
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松本 純一
Exploratory Research Laboratories Dainippon Pharmaceutical Company Ltd.
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木村 嘉孝
Department Of Chemical Technology:dainippon Pharmaceutical Co. Ltd.
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松本 純一
Research Laboratories Dainippon Pharmaceutical Co. Ltd.
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南 新作
Research Laboratories, Dainippon Pharmaceutical Co., Ltd.
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木村 嘉孝
Research Laboratories, Dainippon Pharmaceutical Co., Ltd.
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宮本 皓之
Research Laboratories, Dainippon Pharmaceutical Co., Ltd.
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宮本 皓之
Research Laboratories Dainippon Pharmaceutical Co. Ltd.
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南 新作
大日本製薬株式会社 総合研究所(現):帝国化学産業株式会社研究所
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