Studies on Uricosuric Diuretics. V. Convenient and Efficient Synthesis of 2,3-Dihydrobenzofuran Derivatives
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概要
- 論文の詳細を見る
A practical procedure for synthesis of a new uricosuric agent, 5-chloro-7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid (1,AA-193) is described, which starts from 2,5-dichlorophenol (3b) and involves 5-chloro-6-hydroxy-3-phenyl-1,2-benzisoxazole (2) as the key intermediate. Successive treatment of 3b with benzoyl chloride-aluminum chloride (AlCl_3) and hot ethanolic sodium hydroxide gives 4-benzoyl-2,5-dichlorophenol (8,61%), which is oximated with hydroxylamine hydrochloride and then transformed into the benzisoxazole 2 (88%) with potassium hydroxide in N, N-dimethylformamide (DMF) (method C). The reaction of 2 with aqueous formaldehyde and dimethylamine affords the Mannich base 11a (97%), which is treated with a sulfonium ylide 12,14 or 15 followed by heating with sodium hydroxide (NaOH) in ethanol (EtOH) to give 1 in high yield (method E).
- 社団法人日本薬学会の論文
- 1992-10-25
著者
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佐藤 晴彦
Exploratory Research Laboratories Chugai Pharmaceutical Co. Ltd.
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古賀 弘
Exploratory Research Laboratories Chugai Pharmaceutical Co. Ltd.
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青木 文弥
Exploratory Research Laboratories, Chugai Pharmaceutical Co., Ltd.,
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黒丸 精則
Exploratory Research Laboratories, Chugai Pharmaceutical Co., Ltd.,
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石沢 武宣
Exploratory Research Laboratories, Chugai Pharmaceutical Co., Ltd.,
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青木 文弥
Exploratory Research Laboratories Chugai Pharmaceutical Co. Ltd.
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黒丸 精則
Exploratory Research Laboratories Chugai Pharmaceutical Co. Ltd.
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石沢 武宣
Exploratory Research Laboratories Chugai Pharmaceutical Co. Ltd.
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