79997-20-9Relevant academic research and scientific papers
Synthesis of Dialkyl 5-Amino-2-hydroxy-4,6-dimethylisophthalates and Their Sulfonylation
Povarov,Shilenkov,Peterson,Suboch,Tovbis
, p. 730 - 733 (2019)
Dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate and dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate were obtained in the free form for the first time. The products were sulfonylated with p-toluenesulfonyl to obtain previously unknown dialkyl 5-(4-toluenesulfonamido)-2-hydroxy-4,6-dimethylisophthalates. The use of p-acetamidobenzenesulfonyl chloride as the sulfonylating agent in this reaction led to the formation of dialkyl 5-(4-acetamidobenzenesulfonamido)-2-hydroxy-4,6-dimethyl isophthalates. The synthesized sulfonamide derivatives are of interest as potentially biologically active compounds. The structure of all the obtained compounds was proved using IR and NMR spectroscopy and mass spectrometry.
Synthesis, Acid–Base Properties, and Sulfonylation of Dialkyl 5-Amino-2-hydroxy-4,6-dimethylisophtalates
Krasnov, P. O.,Povarov, I. G.,Shilenkov, N. A.,Suboch, G. A.,Tovbis, M. S.
, p. 1412 - 1420 (2020/10/02)
Abstract: 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 pKa and pKBH+ 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 1H 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.
Catalytic hydrogenation of persubstituted p-nitrosophenols
Slashchinin,Tovbis,Root,Zadov,Sokolenko
experimental part, p. 517 - 519 (2010/08/19)
Catalytic hydrogenation of dialkyl 2-hydroxy-4,6-dimethyl-5-nitrosobenzene- 1,3-dicarboxylates over Pd/C gave the corresponding previously unknown dialkyl 5-amino-2-hydroxy-4,6-dimethylbenzene-1,3-dicarboxylates. The first-order rate constants for the hydrogenation process were found to be linearly related to steric constants of the alkyl groups.
5-Aminoacetamido-4,6-dimethyl-2-hydroxy-isophthalic acid diethyl ester: Synthesis and investigation of antiarrhythmic properties. 92th Comm.: Investigations on pyran derivatives
Eiden,Leister,Mayer
, p. 101 - 105 (2007/10/02)
The 1,3-diacyl-4-pyrones and the 4-pyrone-1,3-dicarboxylic ester respectively, were converted to the substituted nitrophenols on treatment with nitromethane/t-butoxide and subsequently reduced to the aminophenols. The 5-amino-2-hydroxy- (and -2-methoxy-,
