Cyclic tautomers of tryptophans and tryptamines. VI. Preparation of Na-alkyl-,5-chloro-, and 5-nitrotryptophan derivatives.

• 谷口 幹雄

• 權正 晃徳

• 中川 昌子

• 日野 亨

抄録

Selective N_a-alkylation, 5-chlorination, 5-bromination, and 5-nitration of tryptophan derivatives were achieved. The alkylation of the cyclic tautomer 2 of N_b-methoxycarbonyl-DL-tryptophan methyl ester (1) with alkyl halides in acetone-K₂CO₃ gave the N_a-alkyl derivatives (3a and 4) in excellent yields. The chlorination of the cyclic tautomer 3b with NCS-AcOH gave the 5-chloro derivative (5b) in 89% yield, and this was readily converted to the 5-chlorotryptophan derivatives (7a, 7b, 9). The similar chlorination of 12 gave the 5-chloro derivatives (13a, 15a) and the 3a-chloropyrroloindole derivative (17). On the other hand the bromination of 12 with NBS-AcOH gave the 5-bromo derivative (13b) in good yield, and this was readily converted to 15d and further to 15c. The nitration of 3b and 12 with fuming nitric acid also gave the 5-nitro derivatives (5c, 7c, 13c, 15e) in excellent yields.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 31 (6), 1856-1865, 1983

  公益社団法人 日本薬学会

キーワード

• N-bromosuccinimide

詳細情報

• CRID: 1390282679143841152
• NII論文ID: 130003769374
• DOI: 10.1248/cpb.31.1856
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/31/6/31_6_1856/_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