Improved synthesis of quinocetone and its two deoxy metabolites

Yuwen Li, Mei Qiu, Yubin Bai, Shaoqi Qu, Zhihui Hao

Abstract


Oxidation of o-nitroaniline with sodium hypochlorite afforded benzo­furazan oxide in 96 % yield, and treatment of benzofurazan oxide with acetyl­acetone in the presence of triethylamine gave 2-acetyl-3-methyl-quinoxaline-
-1,4-dioxide in 94 % yield. Finally, condensation of 2-acetyl-3-methyl-quinox­aline-1,4-dioxide with benzaldehyde using 4-(dimethylamino)pyridinium ace­tate as a catalyst led to quinocetone in 95 % yield. Subsequently, reduction of the synthesized quinocetone with sodium dithionite resulted in two deoxy derivatives, 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one and 1-(3-methyl-2-quinoxalinyl)-3-phenyl-2-propen-1-one in 88.5 and 92 % yield, respect­ively. Furthermore, the synthesized quinocetone, and its deoxy deri­vatives were characterized by 1H-NMR, 13C-NMR and elem­ental analysis.


Keywords


quinocetone; 1-desoxy quinocetone; 4-(N,N-Dimethylamino)pyri¬dinum acetate; 1,4-didesoxy quinocetone; synthesis

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DOI: https://doi.org/10.2298/JSC170614118L

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