A New Cinnoline Ring Construction by the Reaction of 2-Diazo-3-(2-fluorophenyl)-3-oxopropionates with Tri-n-buthylphosphine
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概要
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A new and convenient synthesis of 4-hydroxycinnoline-3-carboxylate derivatices was developed. Reactions of ethyl 2-diazo-3-(2,4,5-triflurophenyl- and 2,3,4,5-tetrafluorophenyl)-3-oxopropionates (2a and 2c) with tri-n-butylphosphine afforded ethyl 6,7-difluoro- and 6,7,8-trifluoro-4-hydroxycinnoline-3-carboxylates (5a and 5c) and ethyl 2-hydrazono-3-(2,4,5-trifluoro-phenyl- and 2,3,4,5-tetrafluorophenyl)-3-oxopropionates (6a and 6c), respectively. When triphenylphosphine was used, the reaction of 2a-c afforded[[l-ethoxycarbonyl-2-oxo-2-(halogenated phenyl)ethylidene]hydrazono]triphenylphosphoranes (3a-c), which were hydrolyzed to give the corresponding hydrazones 6a-c. An alternate and efficient synthesis of 5a and 5c was accomplished by an intramolecular cyclization of 6a and 6c, respectively. A base-catalyzed cyclization of the methylhydrazone 7 gave ethyl 7-chloro-6-fluoro-1-methyl-1,4-dihydro-4-oxocinnoline-3-carboxylate (8). Possible mechanisms for the reaction of 2 leading to 5 are discussed.
- 公益社団法人日本薬学会の論文
- 1988-04-25
著者
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松本 純一
Exploratory Research Laboratories Dainippon Pharmaceutical Company Ltd.
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松本 純一
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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