Meisenheimer Rearrangement of Azetopyridoindoles. III. Synthesis of 3,6-Epoxyhexahydroazocino[5,4-b]indoles

• 栗原 拓史

  Osaka University of Pharmaceutical Sciences

• 坂本 靖彦

  Osaka University of Pharmaceutical Sciences

• 高井 雅人

  Osaka University of Pharmaceutical Sciences

• 大内 かおり

  Osaka University of Pharmaceutical Sciences

• 春沢 信哉

  Osaka University of Pharmaceutical Sciences

• 米田 龍司

  Osaka University of Pharmaceutical Sciences

抄録

Oxidation of 2-ethylhexahydroazeto[1', 2' : 1,2]pyrido[3,4-b]indole-1-carboxylate 9 with m-chloroperbenzoic acid in methylene dichloride at -5℃ gava the corresponding cis-N-oxide 10,which was spontaneously transformed in tetrahydrofuran to the 3,6-epoxy-1,2,3,4,5,6-hexahydroazocino[5,4-b]indole 11 (75%) via the [1,2]-Meisenheimer rearrangement, along with a formation of the isoxazolidinone 12 (6.4%) through Cope elimination. The structural assignment of azocinoindole 11 was accomplished, mainly based on the ^1H-NMR spectrum and also by chemical transformation of 11 to the azocinoindole 14.

収録刊行物

• Chemical & pharmaceutical bulletin

  Chemical & pharmaceutical bulletin 41 (7), 1221-1225, 1993-07-15

  公益社団法人日本薬学会

キーワード

• Meisenheimer rearrangement
• azetopyridoindole
• epoxyazocinoindole
• isoxazolidinone
• azocinoindole
• Cope elimination

詳細情報

• CRID: 1572824502207884416
• NII論文ID: 110003630590
• NII書誌ID: AA00602100
• ISSN: 00092363
• 本文言語コード: en
• データソース種別:
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