A simple and efficient method for the synthesis of highly substituted imidazoles using 3-aroylquinoxalin-2(1H)-ones |
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| Authors: | Vakhid A Mamedov Nataliya A ZhukovaTat′yana N Beschastnova Aidar T GubaidullinDimitry V Rakov Il’dar Kh Rizvanov |
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| Institution: | A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, Arbuzov Str. 8, 420088 Kazan, Russian Federation |
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| Abstract: | 3-Aroylquinoxalin-2(1H)-ones were found to be hetero analogues of α-diketones for the efficient, one-pot, three component synthesis of 2,4,5-trisubstituted imidazoles and imidazo1,5-a]quinoxalin-4(5H)-ones in boiling methanol. The key advantages of this process are high yields, ready availability and low cost of 3-aroylquinoxalin-2(1H)-ones and easy work-up and separation of the products by non-chromatographic methods. Furthermore, the presence of an ortho-iminoanilide fragment at position 4 of the imidazoles obtained has made it possible to produce 2-(imidazol-4-yl)benzimidazoles in almost quantitative yields. |
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| Keywords: | Multicomponent reaction One-pot synthesis 2 4 5-Trisubstituted imidazoles 3-Aroylquinoxalin-2(1H)-ones Imidazo[1 5-a]quinoxalin-4(5H)-ones Ring formation 2-(Imidazol-4-yl)benzimidazoles NMR data X-ray diffraction analysis |
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