Reactions of pyrazolo(1,5-a)pyrimidine derivatives with nucleophiles. IV. Some reactions of 1,4-dihydrocyclopent(b)indoles.

• 栗原 拓史

• 那須 啓子

• 萩永 里美

• 三原 京子

抄録

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').

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 32 (11), 4410-4418, 1984

  公益社団法人 日本薬学会

キーワード

• bicyclo [2.2.1]-hept [2, 3-b] indole

詳細情報

• CRID: 1390001204167461760
• NII論文ID: 130003769497
• DOI: 10.1248/cpb.32.4410
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/32/11/32_11_4410/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可