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) 


Vol. 30,  No. 4, pp. 389-393, Aug.  1986


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  Abstract

선택적 환원시약인 사카르보닐 철산염(O)을 상압의 일산화탄소하 실온 및 60℃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℃의 고압솥반응에서 N-qoswkf-2,5-디메틸 피로디딘이 보통 수득율로 얻어졌다. 이들 반응의 메카니즘도 검토 하였다. 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℃ 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℃ 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.

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  Cite this article

[IEEE Style]

S. C. Shim, K. T. Huh, K. D. Kim, D. H. Oh, W. S. Kim, "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)," Journal of the Korean Chemical Society, vol. 30, no. 4, pp. 389-393, 1986. DOI: .

[ACM Style]

Sang Chul Shim, Keun Tai Huh, Kee Doo Kim, Dae Hee Oh, and Woo Sik Kim. 1986. 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). Journal of the Korean Chemical Society, 30, 4, (1986), 389-393. DOI: .

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