An efficient method for the synthesis of imidazo[1,5-a]quinoxalines from 3-acylquinoxalinones and benzylamines via a novel imidazoannulation |
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Authors: | Vakhid A Mamedov Aleksey A Kalinin Alsu A Balandina Il'dar Kh Rizvanov Shamil K Latypov |
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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, Kazan 420088, Russian Federation |
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Abstract: | The reaction of 3-aroylquinoxalin-2(1H)-ones and their N-alkyl analogues with benzylamines in DMSO proceeds through an intermediate formation of N-(α-quinoxalinylbenzylydene)benzylamine, which when subjected to oxidative cyclocondensation gives imidazo1,5-a]quinoxalines. Applying this new approach of imidazoannullation to the bis-3-aroylquinoxalines makes it possible to develop fundamentally new methods of the synthesis of bis-imidazo1,5-a]quinoxalines with the use of different benzylamines and heteromacrocycles with the 1,3-bis(3-arylimidazo1,5-a]quinoxalin-1-yl)benzene structural fragment when m-xylylenediamine is used. |
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Keywords: | Quinoxalin-2(1H)-ones Benzylamines Imidazoannellation Imidazo[1 5-a]quinoxalines Macrocyclization Mass spectrometry IR NMR |
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