Reactions of Pyrazolo [1,5-α] pyrimidine Derivatives with Nucleophiles. IV. Some Reactions of 1,4-Dihydrocyclopent [b] indoles

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概要

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• 4,7-Dihydro-4-methyl-7-(N-methyl-3-indolyl) pyrazolo [1,5-α] pyrimidine (3) obtained from pyrazolo [1,5-α] pyrimidine (1) was treated with indole in the presence of an excess of triethyloxonium fluoroborate to give a mixture of 1,4-dihydro-3-(3-indolyl) cyclopent [b] indoles (5,6,7 and 8). The reaction of 6 with potassium hydroxide in ethanol at room temperature gave the 1-hydroxy derivative (10), while under reflux 6 gave 1,4-dihydro-1-oxocyclopent [b] indole (11). Treatment of 6 with formaldehyde gave the 1-hydroxymethyl derivative (13). m-Chloroperbenzoic acid oxidation of 6 afforded the 3,4-dihydrocyclopent [b] indole (14). Furthermore, the reaction of 6 with activated olefins, such as maleic anhydride, maleimide, acrylonitrile and ethyl acrylate under reflux in benzene or acetonitrile gave [4+2] cycloadducts, bicyclo [2.2.1] hept [2,3-b] indoles (17,18,20 and 21), via the 2,4-dihydrocyclopent [b] indole intermediate (6').

• 公益社団法人日本薬学会の論文
• 1984-11-25

著者

• 栗原 拓史

  Osaka University of Pharmaceutical Sciences

• 那須 啓子

  Osaka College of Pharmacy

• 萩永 里美

  Osaka College of Pharmacy

• 三原 京子

  Osaka College of Pharmacy

• 栗原 拓史

  Osaka College Of Pharmacy

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