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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 39, Number 5
JKCSEZ 39(5)
October 20, 1995 

Mechanistic Studies for the Cyclization of t-Amine Substituted Anilines and Their Utilization to the Synthesis of Pyrrolo[1,2-a]benzimidazoquinone Derivatives
Chang-Hee Lee*, Ho-Jin Baik, Kuk-Jin Kim, Kiu-Uk Cho, Kyung Taek Oh
몇 가지 ortho 치환된 방향족 4차 아민 및 아마이드를 합성하여 이들을 열고리화하여 pyrrolo[1,2-a]benzimidazole 유도체를 합성하였다. 고리화에 의해 이미다졸 부분이 생성될 때의 메카니즘을 추정하기 위해 극성이 다른 여러 가지 용매를 사용하여 반응을 시켜 보았으며 이때의 생성물을 분리 확인하였다. 또한 고리화된 화합물의 벤젠고리 부분을 산화시켜 para benzo-퀴논을 합성하였으며 합성과정에서 pyrrolo[1,2-a]benzimidazole 4가 nitration될 때 nitro기의 자리선택성을 화학적인 변환을 통해 확인하였다.

A few t-amine substituted anilines and amides were synthesized and cyclized to pyrrolo[1,2-a]benzimidazole by heating in various solvents having different polarity. Subsequent nitration of cyclized compound followed by reduction and oxidation of resulting amine afforded quinone such as 7 in 14% yield. The formation of imidazole moiety by thermal cyclization was independent on the solvent polarity. The regiochemistry for the nitration of 4 was unambiguously determined by chemical transformation.

408 - 413
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