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

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概要

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• 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.

• 公益社団法人日本薬学会の論文
• 1993-07-15

著者

• 春沢 信哉

  Osaka University of Pharmaceutical Sciences

• 米田 龍司

  Osaka University of Pharmaceutical Sciences

• 栗原 拓史

  大阪薬科大学

• 高井 雅人

  Osaka University of Pharmaceutical Sciences

• 米田 龍司

  Agroscience Research Laboratories Sankyo Co. Ltd.

• 坂本 靖彦

  Osaka College of Pharmacy

• Sakamoto Y

  Alfresa Pharma Co.

• 栗原 拓史

  Osaka College Of Pharmacy

• 大内 かおり

  Osaka University of Pharmaceutical Sciences

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