A search for synthetic routes to tetrabenzylglycoluril

Anastasia A. Sinitsyna; Sergey G. Il’yasov; Maya V. Chikina; Ilia V. Eltsov; Andrey A. Nefedov

doi:10.1007/s11696-019-00941-4

A search for synthetic routes to tetrabenzylglycoluril

Anastasia A. Sinitsyna, Sergey G. Il’yasov, Maya V. Chikina, Ilia V. Eltsov, Andrey A. Nefedov

Research output: Contribution to journal › Article › peer-review

Abstract

In this study, a search for synthetic routes to never-before-seen tetrabenzylglycoluril was made and two synthetic strategies were examined: condensation of 1,3-dibenzylurea with glyoxal, and N-alkylation of glycoluril and its disubstituted derivative. The first synthetic approach furnished only a condensation product, 3,3′-bi(6,8-dibenzyl-2,4-dioxa-9,8-diazabicyclo[3.3.0]octan-7-one, bearing the dioxolane moiety, in 24% yield. The second method in which 2,6-dibenzylglycoluril was reacted with BnCl in acetonitrile in the presence of KOH for 3 h afforded the target product tetrabenzylglycoluril in over 60% yield.

Original language	English
Pages (from-to)	1019-1025
Number of pages	7
Journal	Chemical Papers
Volume	74
Issue number	3
DOIs	https://doi.org/10.1007/s11696-019-00941-4
Publication status	Published - 1 Mar 2020

Keywords

Benzylation
Condensation
Glycoluril
Glyoxal
Tetrabenzylglycoluril

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10.1007/s11696-019-00941-4

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title = "A search for synthetic routes to tetrabenzylglycoluril",

abstract = "In this study, a search for synthetic routes to never-before-seen tetrabenzylglycoluril was made and two synthetic strategies were examined: condensation of 1,3-dibenzylurea with glyoxal, and N-alkylation of glycoluril and its disubstituted derivative. The first synthetic approach furnished only a condensation product, 3,3′-bi(6,8-dibenzyl-2,4-dioxa-9,8-diazabicyclo[3.3.0]octan-7-one, bearing the dioxolane moiety, in 24% yield. The second method in which 2,6-dibenzylglycoluril was reacted with BnCl in acetonitrile in the presence of KOH for 3 h afforded the target product tetrabenzylglycoluril in over 60% yield.",

keywords = "Benzylation, Condensation, Glycoluril, Glyoxal, Tetrabenzylglycoluril",

author = "Sinitsyna, {Anastasia A.} and Il{\textquoteright}yasov, {Sergey G.} and Chikina, {Maya V.} and Eltsov, {Ilia V.} and Nefedov, {Andrey A.}",

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T1 - A search for synthetic routes to tetrabenzylglycoluril

AU - Sinitsyna, Anastasia A.

AU - Il’yasov, Sergey G.

AU - Chikina, Maya V.

AU - Eltsov, Ilia V.

AU - Nefedov, Andrey A.

PY - 2020/3/1

Y1 - 2020/3/1

N2 - In this study, a search for synthetic routes to never-before-seen tetrabenzylglycoluril was made and two synthetic strategies were examined: condensation of 1,3-dibenzylurea with glyoxal, and N-alkylation of glycoluril and its disubstituted derivative. The first synthetic approach furnished only a condensation product, 3,3′-bi(6,8-dibenzyl-2,4-dioxa-9,8-diazabicyclo[3.3.0]octan-7-one, bearing the dioxolane moiety, in 24% yield. The second method in which 2,6-dibenzylglycoluril was reacted with BnCl in acetonitrile in the presence of KOH for 3 h afforded the target product tetrabenzylglycoluril in over 60% yield.

AB - In this study, a search for synthetic routes to never-before-seen tetrabenzylglycoluril was made and two synthetic strategies were examined: condensation of 1,3-dibenzylurea with glyoxal, and N-alkylation of glycoluril and its disubstituted derivative. The first synthetic approach furnished only a condensation product, 3,3′-bi(6,8-dibenzyl-2,4-dioxa-9,8-diazabicyclo[3.3.0]octan-7-one, bearing the dioxolane moiety, in 24% yield. The second method in which 2,6-dibenzylglycoluril was reacted with BnCl in acetonitrile in the presence of KOH for 3 h afforded the target product tetrabenzylglycoluril in over 60% yield.

KW - Benzylation

KW - Condensation

KW - Glycoluril

KW - Glyoxal

KW - Tetrabenzylglycoluril

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