Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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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
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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.

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