Quinoxaline-benzimidazole rearrangement in the synthesis of benzimidazole-based podands |
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Authors: | V A Mamedov A A Kalinin A T Gubaidullin E A Gorbunova I A Litvinov |
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Institution: | (1) Arbuzov Institute of Organic and Physical Chemistry Kazan Research Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia |
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Abstract: | Alkylation of 3-benzoylquinoxalin-2(1H)-one with 1,5-dibromo-3-oxapentane, 1,8-dibromo-3,6-dioxaoctane, and α,ω-dihaloalkanes with different lengths of the polymethylene chain gave the corresponding quinoxaline podands. In the reaction with 1,2-dibromoethane, the N,O-rather than N,N′-alkylation product was obtained. The reaction of the obtained quinoxaline-based podands with benzene-1,2-diamine followed the quinoxaline-benzimidazole rearrangement pattern with formation of 2-(3-phenylquinoxalin-2-yl)benzimidazole-based podands. |
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