Improved synthesis of quinocetone and its two desoxymetabolites

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 3-methyl-2-acetyl-quinoxaline-1,4-dioxide in 94 % yield. Final condensation of 3-methyl-2-acetyl-quinoxaline-1,4-dioxide with benzaldehyde using 4-(N,N-Dimethylamino)pyridinium acetate as a catalyst led to quinocetone  in 95 % yield. Subsequently, reduction of the synthesized quinocetone  with sodium dithionite resulted in 1-desoxy quinocetone  and 1,4-didesoxy quinocetone  in 88.5 % and 92 % yield, respectively. And the synthesized quinocetone, 1-desoxy quinocetone and 1,4-didesoxy quinocetone were characterized by 1HNMR, 13CNMR 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: http://dx.doi.org/10.2298/JSC170614118L

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