565470-69-1Relevant academic research and scientific papers
A simple and efficient method for the synthesis of highly substituted imidazoles using 3-aroylquinoxalin-2(1H)-ones
Mamedov, Vakhid A.,Zhukova, Nataliya A.,Beschastnova, Tatyana N.,Gubaidullin, Aidar T.,Rakov, Dimitry V.,Rizvanov, Il'Dar Kh.
scheme or table, p. 4280 - 4284 (2011/09/12)
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 imidazo[1,5-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.
Fused polycyclic nitrogen-containing heterocycles: IX. Oxidative fusion of imidazole ring to 3-benzoylquinoxalin-2-ones
Mamedov,Kalinin,Gorbunova,Habicher
, p. 1041 - 1046 (2007/10/03)
3-α-Chlorobenzyl- and 3-benzoylquinoxalin-2-ones react with benzylamine in DMSO to give intermediate 3-(α-benzyliminobenzylidene) quinoxalin-2-one which is capable of existing in several tautomeric forms. The subsequent oxidative cyclocondensation leads to imidazo[1,5-a]quinoxalin-4-one. This new procedure for building up imidazo[1,5-a]quinoxalin-4-one system has been applied to the synthesis of various bis(imidazo[1,5-a]quinoxalin-4-ones).
Fused Nitrogen-Containing Heterocycles: III. 4-Oxo-1-phenyl-4,5- dihydroimidazo[1,5-a]quinoxalines. A Retrosynthetic Approach
Mamedov,Kalinin,Azancheev,Levin
, p. 125 - 130 (2007/10/03)
Retrosynthetic analysis of the structure of imidazo[1,5-a]quinoxalines made it possible to develop new convenient procedures for preparation of these compounds by reaction of 3-(α-chlorobenzyl)-1,2-dihydroquinoxalin-2-one with potassium thiocyanate or isocyanate as synthetic equivalent of the two-membered N-=C+ building blocks and by reaction of 3-(α-aminobenzyl)-1,2-dihydroquinoxalin-2-one with carbon disulfide, triethoxymethane, aromatic aldehydes, or acetic anhydride as synthetic equivalent of the one-membered RC3+ synthon.
