A search for synthetic routes to tetrabenzylglycoluril
Anastasia A Sinitsyna
1
,
Sergey Il’yasov
1
,
Maya V Chikina
1
,
Ilia V Eltsov
2
,
Andrey A Nefedov
2, 3
Publication type: Journal Article
Publication date: 2019-09-21
scimago Q2
wos Q3
SJR: 0.431
CiteScore: 4.3
Impact factor: 2.5
ISSN: 03666352, 13369075, 25857290
Materials Chemistry
General Chemistry
Biochemistry
General Chemical Engineering
Industrial and Manufacturing Engineering
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.
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Sinitsyna A. A. et al. A search for synthetic routes to tetrabenzylglycoluril // Chemical Papers. 2019. Vol. 74. No. 3. pp. 1019-1025.
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Sinitsyna A. A., Il’yasov S., Chikina M. V., Eltsov I. V., Nefedov A. A. A search for synthetic routes to tetrabenzylglycoluril // Chemical Papers. 2019. Vol. 74. No. 3. pp. 1019-1025.
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RIS
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TY - JOUR
DO - 10.1007/s11696-019-00941-4
UR - http://link.springer.com/10.1007/s11696-019-00941-4
TI - A search for synthetic routes to tetrabenzylglycoluril
T2 - Chemical Papers
AU - Sinitsyna, Anastasia A
AU - Il’yasov, Sergey
AU - Chikina, Maya V
AU - Eltsov, Ilia V
AU - Nefedov, Andrey A
PY - 2019
DA - 2019/09/21
PB - Springer Nature
SP - 1019-1025
IS - 3
VL - 74
SN - 0366-6352
SN - 1336-9075
SN - 2585-7290
ER -
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BibTex (up to 50 authors)
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@article{2019_Sinitsyna,
author = {Anastasia A Sinitsyna and Sergey Il’yasov and Maya V Chikina and Ilia V Eltsov and Andrey A Nefedov},
title = {A search for synthetic routes to tetrabenzylglycoluril},
journal = {Chemical Papers},
year = {2019},
volume = {74},
publisher = {Springer Nature},
month = {sep},
url = {http://link.springer.com/10.1007/s11696-019-00941-4},
number = {3},
pages = {1019--1025},
doi = {10.1007/s11696-019-00941-4}
}
Cite this
MLA
Copy
Sinitsyna, Anastasia A., et al. “A search for synthetic routes to tetrabenzylglycoluril.” Chemical Papers, vol. 74, no. 3, Sep. 2019, pp. 1019-1025. http://link.springer.com/10.1007/s11696-019-00941-4.
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