Synthesis of 1-[1-(diphenoxyphosphoryl)alkyl]-3,4,6-trimethylglycolurils

Gorbin, Sergey I.; Bakibaev, Abdigali A.; Kurgachev, Dmitryi A.; Malkov, Victor S.; Novolokov, Kirill Yu.; Sysoev, Gleb O.

doi:10.1016/j.mencom.2023.09.015

Cited by 2 publications

(1 citation statement)

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“…However, these reports are sporadic, and to date, only a relatively small number of synthetic approaches have been developed for preparing phosphoruscontaining glycoluril derivatives [16][17][18][19], and the main regularities of the formation of stereoisomers of the phosphonate derivatives of glycoluril have not been established either. We previously found [20] that the interaction of 1,3,4-trimethylglycoluril with aliphatic aldehydes and triphenylphosphite in acetonitrile using methanesulfonic acid as a catalyst led to the formation of 1-[1-(diphenylphosphono)alkyl]-3,4,6-trimethylglycoluril.…”

Section: Introductionmentioning

confidence: 99%

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

Gorbin,

Bakibaev,

Tuguldurova

et al. 2023

IJMS

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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.

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