Synthesis of Novel Phosphorus-Containing Derivatives of 1,3,4-Trimethylglycoluril via the Birum–Oleksyszyn Reaction

Synthesis of Novel Phosphorus-Containing Derivatives of 1,3,4-Trimethylglycoluril via the Birum–Oleksyszyn Reaction Full article

Journal

International Journal of Molecular Sciences
ISSN: 1661-6596 , E-ISSN: 1422-0067

Output data

Year: 2023, Volume: 24, Number: 23, Article number : 17082, Pages count : 16 DOI: 10.3390/ijms242317082

Authors

Gorbin Sergey I. ¹ , Bakibaev Abdigali A. ¹ , Tuguldurova Vera P. ¹ , Kotov Andrey V. ¹ , Sysoev Gleb O. ¹ , Potapov Andrei S. ² , Pavlov Dmitry I. ² , Malkov Victor S. ¹ , Knyazev Alexey S. ¹ , Kurgachev Dmitriy A. ¹ , Michalchenkov Mark V. ¹

Affiliations

1	Tomsk State University
2	Nikolaev Institute of Inorganic Chemistry

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.

Gorbin S.I. , Bakibaev A.A. , Tuguldurova V.P. , Kotov A.V. , Sysoev G.O. , Potapov A.S. , Pavlov D.I. , Malkov V.S. , Knyazev A.S. , Kurgachev D.A. , Michalchenkov M.V.
Synthesis of Novel Phosphorus-Containing Derivatives of 1,3,4-Trimethylglycoluril via the Birum–Oleksyszyn Reaction
International Journal of Molecular Sciences. 2023. V.24. N23. 17082 :1-16. DOI: 10.3390/ijms242317082 WOS Scopus РИНЦ OpenAlex

Submitted:	Sep 13, 2023
Accepted:	Nov 23, 2023
Published online:	Dec 3, 2023
Published print:	Dec 24, 2023

Web of science:	WOS:001116159000001
Scopus:	2-s2.0-85179355344
Elibrary:	65423051
OpenAlex:	W4389286197

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