Improved synthesis of quinocetone and its two deoxy metabolites

Main Article Content

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.

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How to Cite
[1]
Y. Li, M. Qiu, Y. Bai, S. Qu, and Z. Hao, “Improved synthesis of quinocetone and its two deoxy metabolites”, J. Serb. Chem. Soc., vol. 83, no. 3, pp. 265–270, Apr. 2018.
Section
Organic Chemistry

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