Synthesis, Acid–Base Properties, and Sulfonylation of Dialkyl 5-Amino-2-hydroxy-4,6-dimethylisophtalates

Dialkyl 5-amino-2-hydroxy-4,6-dimethylisophthalates were synthesized for the first time by the reduction of the corresponding nitroso derivatives with sodium dithionite. The p K a and p K BH+ values of the synthesized compounds were determined and taken into account to find conditions for their sulf...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2020-08, Vol.56 (8), p.1412-1420
Main Authors: Povarov, I. G., Shilenkov, N. A., Krasnov, P. O., Suboch, G. A., Tovbis, M. S.
Format: Article
Language:English
Subjects:
Antiinfectives and antibacterials
Chemistry
Chemistry and Materials Science
Chlorides
Derivatives
Infrared spectroscopy
Mass spectrometry
NMR spectroscopy
Organic Chemistry
Sodium dithionite
Synthesis
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Summary:Dialkyl 5-amino-2-hydroxy-4,6-dimethylisophthalates were synthesized for the first time by the reduction of the corresponding nitroso derivatives with sodium dithionite. The p K a and p K BH+ values of the synthesized compounds were determined and taken into account to find conditions for their sulfonylation with p -toluenesulfonyl chloride and p -acetamidobenzenesulfonyl chloride. As a result, previously unknown sulfonylated derivatives of substituted aminoisophthalates with potential antimicrobial properties were obtained. The composition and structure of the products were confirmed by IR, UV, and 1 H NMR spectroscopy and mass spectrometry. The geometric structure of the sulfonylated compounds was established by DFT calculations at the BP86-D3/def2-SVP level of theory. The antibacterial effect of 5-(4-acetamidobenzenesulfonamido)-2-hydroxy-4,6-dimethylisophthalate was revealed.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428020080126