- Rearrangement of quinoxalin-2-ones when exposed to enamines generated in situ from ketones and ammonium acetate: method for the synthesis of 1-(pyrrolyl)benzimidazolones.
Rearrangement of quinoxalin-2-ones when exposed to enamines generated in situ from ketones and ammonium acetate: method for the synthesis of 1-(pyrrolyl)benzimidazolones.
The Journal of organic chemistry (2014-12-17)
Vakhid A Mamedov, Nataliya A Zhukova, Tat'yana N Beschastnova, Victor V Syakaev, Dmitry B Krivolapov, Ekaterina V Mironova, Anastasiya I Zamaletdinova, Il'dar Kh Rizvanov, Shamil K Latypov
PMID25496019
ABSTRACT
The reaction of 3-benzoylquinoxalin-2(1H)-ones with enamines (generated in situ from ammonium acetate and the corresponding methylaryl(hetaryl)ketones) proceeds smoothly to give the corresponding substituted 1-(pyrrolyl)benzimidazolone derivatives in moderate yields through the novel rearrangement of 3-benzoylquinoxalin-2(1H)-ones involving a dual cleavage of the C3═N4 and C2-C3 bonds under mild conditions.
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N,N-dimetilformammide, Pharmaceutical Secondary Standard; Certified Reference Material