Synthesis of Novel Phosphorus-Containing Derivatives of 1,3,4-Trimethylglycoluril via the Birum–Oleksyszyn Reaction
-
Published:2023-12-03
Issue:23
Volume:24
Page:17082
-
ISSN:1422-0067
-
Container-title:International Journal of Molecular Sciences
-
language:en
-
Short-container-title:IJMS
Author:
Gorbin Sergey I.1, Bakibaev Abdigali A.1, Tuguldurova Vera P.1ORCID, Kotov Andrey V.1ORCID, Sysoev Gleb O.1, Potapov Andrei S.2ORCID, Pavlov Dmitry I.2ORCID, Malkov Victor S.1ORCID, Knyazev Alexey S.1, Kurgachev Dmitriy A.1, Michalchenkov Mark V.1
Affiliation:
1. Department of Chemistry, Tomsk State University, 36, Lenin Avenue, Tomsk 634050, Russia 2. Nikolaev Institute of Inorganic Chemistry, 3 Lavrentiev Avenue, Novosibirsk 630090, Russia
Abstract
This work presents the synthesis of a new compound, 1-[aryl-(diphenylphosphono)methyl]-3,4,6-trimethylglycolurils, via the interaction of benzaldehyde and its mononitro- and monohydroxyderivatives with 1,3,4-trimethylglycoluril and triphenylphosphite. By varying the reaction conditions and the catalysts, the obtained product yields ranged from satisfactory to good. The diastereomers formed during the reaction were separated by semipreparative HPLC on the C18 stationary phase. The isolated diastereomers were characterized by 1H, 13C, and 31P NMR, and the structures of the diastereomers were confirmed using a single-crystal X-ray crystal structure analysis and quantum chemical calculations.
Funder
National Research Tomsk State University
Subject
Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Computer Science Applications,Spectroscopy,Molecular Biology,General Medicine,Catalysis
Reference30 articles.
1. Correlations between the self-organization, physicochemical properties and biological activity of Mebicar in dilute aqueous solutions;Ryzhkina;Mendeleev Commun.,2013 2. Neuroprotective Activity of (+)-(S)-2-[(1S,5R)-(3,7-Dioxo-2,4,6,8-Tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid;Kravchenko;Russ. J. Bioorg. Chem.,2012 3. Steinhauer, K., Beilfus, W., Krull, I., and Gradtke, R. (2006). Verwendung von Formaldehyd und Formaldehyd Freisetzenden Verbindungen in einer Zusammensetzung zur Bekämpfung von Mykobakterien. (102004059041), DE Patent. 4. Mcbride, R., Elsmore, R., and Houghton, M.P. (2001). Bactericide Combinations in Detergents. (2354771), GB Patent. 5. Bambusuril Anion Receptors;Lizal;Isr. J. Chem.,2018
|
|