Improved synthesis of quinocetone and its two desoxymetabolites

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-quinoxali...

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Bibliographic Details
Published in:Journal of the Serbian Chemical Society 2018, Vol.83 (3), p.265-270
Main Authors: Li, Yuwen, Qiu, Mei, Bai, Yubin, Qu, Shaoqi, Hao, Zhihui
Format: Article
Language:English
Subjects:
4-(dimethylamino)pyridinum acetate
desoxy quinocetone
didesoxy quinocetone
quinocetone
synthesis
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Summary: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. nema
ISSN:0352-5139
1820-7421
DOI:10.2298/JSC170614118L