Improved synthesis of quinocetone and its two desoxymetabolites

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.