Reactions of Pyrazolo [1,5-a] pyrimidine Derivatives with Nucleophiles. III. Nucleophilic Addition to 6,7-Bis (ethoxycarbonyl) pyrazolo [1,5-a] pyrimidine-3-carbonitrile in the Presence of Triethyloxonium Fluoroborate

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概要

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• Nucleophilic additions of phenol and aniline analogs to 6,7-bis (ethoxycarbonyl) pyrazolo [1,5-a] pyrimidine-3-carbonitrile (1) in the presence of triethyloxonium fluoroborate are described. For example, though phenol or o-cresol (having no substituent at the para-position) reacted with 1 to give the cyclohexadienylidene derivatives (3,4), p- or m-cresols, p-methoxyphenol, and α-or β-naphthol gave the corresponding spiro lactones (6,7,8,10 and 12). When 1 was treated with several kinds of aniline analogs, three types of products were obtained. Namely, while aniline or o-toluidine gave the 7-(4-aminophenyl) adducts (13,15), p-anisidine, p-chloroaniline or p-nitroaniline afforded the 7-anilino derivatives (17,20 or 21). Treatment of p-toluidine with 1 under the same reaction conditions gave a mixture of the spiro-indole-3 (2H), 7'(4'H)-pyrazolo [1,5-a] pyrimidin-2-one (22) and the pyrazolo [1', 5' : 1,2] pyrimido [5,6-c] quinoline (23).

• 公益社団法人日本薬学会の論文
• 1982-08-25

著者

• 栗原 拓史

  Osaka University of Pharmaceutical Sciences

• 那須 啓子

  Osaka College of Pharmacy

• 栗原 拓史

  Osaka College Of Pharmacy

関連論文

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