Improved synthesis of quinocetone and its two deoxy metabolites

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

doi:10.2298/JSC170614118L

PDF (891 kB) Supplementary Material (2,15 MB)

Published: Apr 1, 2018

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

Keywords:

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

Yuwen Li

Agricultural Bio-pharmaceutical Laboratory, Qingdao Agricultural University, Qingdao266109 and National-Local Joint Engineering Laboratory of Agricultural Bio-pharmaceutical Technology, Qingdao 266109

Mei Qiu

Agricultural Bio-pharmaceutical Laboratory, Qingdao Agricultural University, Qingdao266109 and National-Local Joint Engineering Laboratory of Agricultural Bio-pharmaceutical Technology, Qingdao 266109

Yubin Bai

Agricultural Bio-pharmaceutical Laboratory, Qingdao Agricultural University, Qingdao266109 and National-Local Joint Engineering Laboratory of Agricultural Bio-pharmaceutical Technology, Qingdao 266109

Shaoqi Qu

Agricultural Bio-pharmaceutical Laboratory, Qingdao and National-Local Joint Engineering Laboratory of Agricultural Bio-pharmaceutical Technology, Qingdao 266109

Zhihui Hao

Agricultural Bio-pharmaceutical Laboratory, Qingdao Agricultural University, Qingdao 266109 and National-Local Joint Engineering Laboratory of Agricultural Bio-pharmaceutical Technology, Qingdao 266109

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.

Issue

Vol. 83 No. 3 (2018)

Section

Organic Chemistry

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