Reaction of 3-Hydrazinylquinoxaline-2(1H)-one with 2-Hydroxyimino-1,3-dicarbonyl Compounds

3-Hydrazinylquinoxalin-2(1 H )-one reacts with ethyl 2-hydroxyimino-3-oxobutanoate or 1-Ar-2-(hydroxyimino)-butane-1,3-diones (Ar = Ph, 4-Me-C 6 H 4 , 4-F-C 6 H 4 , 4-Cl-C 6 H 4 , 4-Br-C 6 H 4 , naphthalen-1-yl) in acetic acid to form a mixture of the E- and Z- hydrazones in excellent yields. The re...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2022-11, Vol.58 (11), p.1628-1636
Main Authors: Bobrov, P. S., Semichenko, E. S., Kondrasenko, A. A., Suboch, G. A.
Format: Article
Language:English
Subjects:
Acetic acid
Carbonyl compounds
Chemical analysis
Chemistry
Chemistry and Materials Science
Diketones
Ethanol
Hydrazones
Mass spectrometry
NMR spectroscopy
Organic Chemistry
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Summary:3-Hydrazinylquinoxalin-2(1 H )-one reacts with ethyl 2-hydroxyimino-3-oxobutanoate or 1-Ar-2-(hydroxyimino)-butane-1,3-diones (Ar = Ph, 4-Me-C 6 H 4 , 4-F-C 6 H 4 , 4-Cl-C 6 H 4 , 4-Br-C 6 H 4 , naphthalen-1-yl) in acetic acid to form a mixture of the E- and Z- hydrazones in excellent yields. The reaction of 3-hydrazinylquinoxalin-2(1 H )-one with 1-(pyridin-4-yl)-2-(hydroxyimino)butane-1,3-dione gave 3-[5-hydroxy-4-(hydroxyimino)-3-methyl-5-(pyridin-4-yl)-4,5-dihydro-1 H -pyrazol-1-yl]quinoxalin-2(1 H )-one. The reaction with 2-hydroxyimino-3-oxobutanal in ethanol leads to 3-{2-[2-(hydroxyimino)-3-oxobutylidene]hydrazinyl}quinoxalin-2(1 H )-one. The structures of the synthesized compounds were determined by UV–Vis, IR, and 1 H and 13 C NMR spectroscopy, chromatography–mass spectrometry, and elemental analysis. Proton signals were assigned using 2D homo- ( 1 H– 1 H COSY) and heteronuclear ( 1 H– 13 C HSQC, 1 H– 13 C HMBC, 1 H– 15 N HMBC) experiments.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428022110100