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

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.

SUBMITTER: Gorbin SI

PROVIDER: S-EPMC10707106 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature

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

Gorbin Sergey I SI Bakibaev Abdigali A AA Tuguldurova Vera P VP Kotov Andrey V AV Sysoev Gleb O GO Potapov Andrei S AS Pavlov Dmitry I DI Malkov Victor S VS Knyazev Alexey S AS Kurgachev Dmitriy A DA Michalchenkov Mark V MV

International journal of molecular sciences 20231203 23

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 diaste ...[more]

PMID: 38069405

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Synthesis and antifungal activities of novel nicotinamide derivatives containing 1,3,4-oxadiazole.

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Design, synthesis and antimicrobial activities of novel 1,3,5-thiadiazine-2-thione derivatives containing a 1,3,4-thiadiazole group.

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| S-EPMC6733239 | biostudies-literature

Design, synthesis, insecticidal activity and 3D-QSR study for novel trifluoromethyl pyridine derivatives containing an 1,3,4-oxadiazole moiety.

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Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides.

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