Journal of the Korean Chemical Society (대한화학회지)
- Volume 39 Issue 5
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- Pages.408-413
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- 1995
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- 1017-2548(pISSN)
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- 2234-8530(eISSN)
Mechanistic Studies for the Cyclization of t-Amine Substituted Anilines and Their Utilization to the Synthesis of Pyrrolo[1,2-a]benzimidazoquinone Derivatives
4차 아민이 치환된 아닐린의 고리화반응 메카니즘 및 Pyrrolo[1,2-a]benzimidazoquinone 유도체의 합성에의 응용
- Lee, Chang-Hee (Department of Chemistry, Kang Won National University) ;
- Baik, Ho-Jin (Department of Chemistry, Kang Won National University) ;
- Kim, Kuk-Jin (Department of Chemistry, Kang Won National University) ;
- Cho, Kiu-Uk (Department of Chemistry, Kang Won National University) ;
- Oh, Kyung Taek (Department of Chemistry, Kang Won National University)
- 이창희 (강원대학교 자연과학대학 화학과) ;
- 백호진 (강원대학교 자연과학대학 화학과) ;
- 김국진 (강원대학교 자연과학대학 화학과) ;
- 조규욱 (강원대학교 자연과학대학 화학과) ;
- 오경택 (강원대학교 자연과학대학 화학과)
- Published : 19950500
Abstract
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.
Keywords