Amino acids and peptides. XXVII. A novel reductive cleavage of N-C-N bonds with sodium borohydride.

• 村戸 和夫

• 塩入 孝之

• 山田 俊一

抄録

(3S)-tert-Butyl 2-benzyloxycarbonyl-1, 2, 3, 4-tetrahydro-β-carboline-3-carbamate (III), prepared by the modified Curtius reaction of (3S)-2-benzyloxycarbonyl-1, 2, 3, 4-tetrahydro-β-carboline-3-carboxylic acid (II) with diphenyl phosphorazidate (DPPA) and triethylamine in tert-butyl alcohol, afforded 2-ethyloxycarbonylaminomethyl-3-(2-tert-butyloxy-carbonylamino) ethylindole (Va) by sodium borohydride reduction in ethanol, while reduction in 2-propanol gave the corresponding 2-propyl derivative (Vb) and the compound (VI) containing a novel diazocinoindole skeleton. The mechanism of the reductive cleavage was discussed. Tetrahydropyrrole analog (X) of III and 2-acetyl analog of III afforded the similar ring-cleavage products (XI and XV) by sodium borohydride reduction.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 25 (7), 1559-1565, 1977

  公益社団法人 日本薬学会

キーワード

• sodium borohydride reduction

詳細情報

• CRID: 1390001204169437568
• NII論文ID: 110003622612
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.25.1559
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/25/7/25_7_1559/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1978031520
• 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