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

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 catal...

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Bibliographic Details
Published in:International journal of molecular sciences 2023-12, Vol.24 (23), p.17082
Main Authors: Gorbin, Sergey I, Bakibaev, Abdigali A, Tuguldurova, Vera P, Kotov, Andrey V, Sysoev, Gleb O, Potapov, Andrei S, Pavlov, Dmitry I, Malkov, Victor S, Knyazev, Alexey S, Kurgachev, Dmitriy A, Michalchenkov, Mark V
Format: Article
Language:English
Subjects:
1,3,4-trimethylglycoluril
Acids
aryldiphenylphosphonates
Birum–Oleksyszyn reaction
Crystals
Diastereomers
Phosphorus
Solvents
Structure
Temperature
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Summary: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 H, C, and P NMR, and the structures of the diastereomers were confirmed using a single-crystal X-ray crystal structure analysis and quantum chemical calculations.
ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms242317082