Regioselective Displacement Reactions of 1-Cyclopropyl-5,6,7,8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylic Acid with Amine Nucleophiles
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概要
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The displacement reactions of ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-4(1H)-oxoquinoline-3-carboxylate (7) and its carboxylic acid 8 with amine nucleophiles were examined. The nucleophilic displacement occurred regioselectively at the C-5 or C-7 position depending on the substrate (7 or 8) and solvent selected; this finding permitted the introduction of an optional nucleophile preferentially into the required position at either C-5 or C-7,or into both positions with a desired combination of nucleophiles. Taking advantage of this regioselectivity, we prepared various 5-substituted 6,7,8-trifluoro- and 7-substituted 5,6,8-trifluoro-1-cyclopropyl-4(1H)-oxoquinoline-3-carboxylic acids. Furthermore, the use of the boron-chelated derivative of the carboxylic acid 8 was favorable for the regioselective synthesis of 7-substituted 5,6,8-trifluoroquinolones.
- 公益社団法人日本薬学会の論文
- 1990-09-25
著者
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松本 純一
Exploratory Research Laboratories Dainippon Pharmaceutical Company Ltd.
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西村 由郎
Research Laboratories, Dainippon Pharmaceutical Co., Ltd.,
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柴森 厚一郎
Research Laboratories, Dainippon Pharmaceutical Co., Ltd.,
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中野 純次
Research Laboratories, Dainippon Pharmaceutical Co., Ltd.,
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Matsumoto J
Discovery Research Laboratories Ii Dainippon Pharmaceutical Company Ltd.
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松本 純一
Research Laboratories Dainippon Pharmaceutical Co. Ltd.
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Miyamoto Tomofumi
Graduate School Of Pharmaceutical Sciences Kyushu Univ.
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中野 純次
Exploratory Research Laboratories, Dainippon Pharmaceutical Company, Ltd.,
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糸川 彰
Research Laboratories
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宮本 皓之
Research Laboratories, Dainippon Pharmaceutical Co., Ltd.
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糸川 彰
Exploratory Research Laboratories, Dainippon Pharmaceutical Co., Ltd.
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江川 宏
Research Laboratories Dainippon Pharmaceutical Co., Ltd.,
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江川 宏
Exploratory Research Laboratories Dainippon Pharmaceutical Company Ltd.
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西村 由郎
Research Laboratories Dainippon Pharmaceutical Co. Ltd.
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中野 純次
Exploratory Research Laboratories Dainippon Pharmaceutical Company Ltd.
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中野 純次
大日本製薬株式会社総合研究所
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中野 純次
Research Laboratories Dainippon Pharmaceutical Co. Ltd.
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柴森 厚一郎
Research Laboratories Dainippon Pharmaceutical Co. Ltd.
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Egawa H
Showa College Of Pharmaceutical Sciences
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宮本 皓之
Research Laboratories Dainippon Pharmaceutical Co. Ltd.
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Maruta Tomoki
Graduate School Of Pharmaceutical Sciences Kyushu University
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糸川 彰
Exploratory Research Laboratories Dainippon Pharmaceutical Co. Ltd.
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