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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 30, Number 4
JKCSEZ 30(4)
August 20, 1986 

 
Title
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
Author
Sang Chul Shim, Keun Tai Huh, Kee Doo Kim, Dae Hee Oh, Woo Sik Kim

심상철, 허근태, 김기두, 오대희, 김우식
Keywords
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.

Page
389 - 393
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