The Facile Synthesis of N-Substituted 2,5-Dimethylpyrrolidine Derivatives from 2,5-Hexanedione and a Variety of Primary Amines using Tetracarbonylhydridoferrate(O) as a Selective Reducing Agent (II)

선택적 환원시약인 사카르보닐 철산염(O)을 이용한 N-치환-2,5-디메틸 피로리딘 유도체의 용이한 합성

  • Sang Chul Shim (Department of Industrial Chemistry, Kyungpook National University) ;
  • Keun Tai Huh (Department of Industrial Chemistry, Kyungpook National University) ;
  • Kee Doo Kim (Research and Developemnt Center, SamSung Electron Ltdl.,) ;
  • Woo Sik Kim (Department of Industrial Chemistry, Kyungpook National University)
  • 심상철 (경북대학교 공과대학 공업화학과) ;
  • 허근태 (경북대학교 공과대학 공업화학과) ;
  • 김기두 (삼성전관 공업주식회사 종합연구소) ;
  • 김우식 (경북대학교 공과대학 공업화학과)
  • Published : 1986.08.20

Abstract

The reaction of 2,5-hexanedione with a variety of primary amines using tetracarbonylhydridoferrate(O) as a selective reducing agent at room temperature or 60${\circ}C$ under an atmosphere of carbon monoxide gave the corresponding N-substituted 2,5-dimethylpyrrolidine derivatives. The reaction of synthesized 5-nitro-2-hexanone with benzaldehyde in the presence of tetracarbonylhydridoferrate(O) at 150${\circ}C$ under an atmosphere of carbon monoxide in an autoclave also gave N-benzyl-2,5-dimethylpyrrolidine in moderate yield. The mechanism of these reactions was investigated.

선택적 환원시약인 사카르보닐 철산염(O)을 상압의 일산화탄소하 실온 및 60${\circ}C$에서 2,5헥산디온과 각종 일차아민과 반응시켜 대응하는 N-치환 2,5-디메틸 피로리딘 유도체를 좋은 수득율로 얻을 수 있었다. 또한 미리 합성된 5-nitro-2-hexanone과 벤즈알데히드는 사카르보닐 철산염의 존재하, 상압의 일산화탄소, 150${\circ}C$의 고압솥반응에서 N-qoswkf-2,5-디메틸 피로디딘이 보통 수득율로 얻어졌다. 이들 반응의 메카니즘도 검토 하였다.

Keywords

References

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