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KMID : 1059519950390050408
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Journal of the Korean Chemical Society
1995 Volume.39 No. 5 p.408 ~ p.413
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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
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Lee Chang-Hee
Baek Ho-Jin
Kim Kuk-Jin
Cho Kiu-Uk
Oh Kyung-Taek
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Abstract
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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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