A search for synthetic routes to tetrabenzylglycoluril

A search for synthetic routes to tetrabenzylglycoluril Full article

Journal

Chemical Papers
ISSN: 0366-6352 , E-ISSN: 1336-9075

Output data

Year: 2020, Volume: 74, Number: 3, Pages: 1019-1025 Pages count : 7 DOI: 10.1007/s11696-019-00941-4

Tags

Glycoluril; Glyoxal; Condensation; Benzylation; Tetrabenzylglycoluril

Authors

Sinitsyna Anastasia A. ¹ , Il'yasov Sergey G. ¹ , Chikina Maya V. ¹ , Eltsov Ilia V. ² , Nefedov Andrey A. ^2,3

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, Inst Problems Chem & Energet Technol, Lab HighEnergy Cpds Synth, Biisk 659322, Altai Krai, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, Novosibirsk Organ Chem Inst, NIOCh, Novosibirsk 630090, Russia

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.

Sinitsyna A.A. , Il'yasov S.G. , Chikina M.V. , Eltsov I.V. , Nefedov A.A.
A search for synthetic routes to tetrabenzylglycoluril
Chemical Papers. 2020. V.74. N3. P.1019-1025. DOI: 10.1007/s11696-019-00941-4 WOS Scopus

Published online:	Sep 21, 2019
Published print:	Mar 1, 2020

Web of science	WOS:000520152200027
Scopus	2-s2.0-85074005719
OpenAlex	W2974666630