International Journal of New Chemistry
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Synthesis of (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxy-5-((E)-o-tolyldiazenyl)phenyl)prop-2-en-1-one and (E)-2-(4-(dimethylamino) phenyl)-6-(o-tolyldiazenyl)-4H-chromen-4-one

Document Type : Research Paper

Author

hadi A khdera

Tishreen University

https://doi.org/10.22034/ijnc.2024.2030043.1394
Abstract
A new azochalcone derivative (5) (E)-3-(4-(dimethylamino) phenyl) -1- (2-hydroxy -5- ((E) -o- tolyl diazenyl) phenyl) prop-2-en-1-one was synthesized through the reaction of diazotization and coupling of the aromatic amine 2- methyl aniline with the chalcone compound (E) -3- (4-(dimethylamino) phenyl) -1- (2-hydroxyphenyl)prop-2-en-1-one in the presence of sodium nitrite And hydrochloric acid. A new azoflavone derivative (6) (E) -2- (4-(dimethyl amino) phenyl)-6-(o-tolyl diazenyl) -4H- chromen -4- one was also synthesized with high yield through the cyclization reaction of the compound azo chalcone (5) using iodine in dimethyl sulfoxide (DMSO). The chemical structures of the two new compounds were confirmed by spectroscopic methods (13C-NMR, 1HNMR, FT-IR). The biological activity of the two compounds (5 , 6) was investigated at two different concentrations (0.5 mg/ml, 0.25 mg/ml) on three fungal species (Penicillium expansum, Acremonium strictum and Aspergillus flavus) and compared with clotrimazole as a standard antifungal. These compounds showed good activity against the tested fungi, and were most effective on the fungal species Acremonium strictum.

Keywords

Azo chalcone
Azo flavone
Diazotization-Coupling reaction
Fungi
Cyclization
Subjects
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International Journal of New Chemistry
Volume 12, Issue 3
Winter 2025
Pages 474-484

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