Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[ d[[1,3]diazepinones
Almir S. Gazizov
1
,
Nazerke K Otegen
2
,
Julia K Voronina
3, 4
,
Anna G Strelnik
1
,
Aida I Samigullina
1
,
Alexander R Burilov
1
,
Michail A. Pudovik
1
1
Publication type: Journal Article
Publication date: 2020-06-10
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
Imidazolidin-2-one and 1,3-benzodiazepin-2-one scaffolds are structural motifs of many biologically active compounds. Herein, we report a highly regioselective acid-catalyzed intramolecular nucleophilic cyclization/intermolecular electrophilic substitution reaction sequence of (2,2-dialkoxyethyl)ureas. The reaction benefits from readily available starting materials, a simple workup procedure, moderate to high yields of target compounds, and provides a convenient entry to previously unknown 4-(het)arylimidazolidinones and 5-(het)arylbenzodiazepinones. The proposed mechanism of the reaction is also discussed.
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Total citations:
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Citations from 2025:
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Smolobochkin A. V. et al. Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[ d[[1,3]diazepinones // Synthesis. 2020. Vol. 52. No. 21. pp. 3263-3271.
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Smolobochkin A. V., Gazizov A. S., Otegen N. K., Voronina J. K., Strelnik A. G., Samigullina A. I., Burilov A. R., Pudovik M. A. Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[ d[[1,3]diazepinones // Synthesis. 2020. Vol. 52. No. 21. pp. 3263-3271.
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TY - JOUR
DO - 10.1055/s-0040-1707864
UR - https://doi.org/10.1055/s-0040-1707864
TI - Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[ d[[1,3]diazepinones
T2 - Synthesis
AU - Smolobochkin, Andrey V.
AU - Gazizov, Almir S.
AU - Otegen, Nazerke K
AU - Voronina, Julia K
AU - Strelnik, Anna G
AU - Samigullina, Aida I
AU - Burilov, Alexander R
AU - Pudovik, Michail A.
PY - 2020
DA - 2020/06/10
PB - Georg Thieme Verlag KG
SP - 3263-3271
IS - 21
VL - 52
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2020_Smolobochkin,
author = {Andrey V. Smolobochkin and Almir S. Gazizov and Nazerke K Otegen and Julia K Voronina and Anna G Strelnik and Aida I Samigullina and Alexander R Burilov and Michail A. Pudovik},
title = {Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[ d[[1,3]diazepinones},
journal = {Synthesis},
year = {2020},
volume = {52},
publisher = {Georg Thieme Verlag KG},
month = {jun},
url = {https://doi.org/10.1055/s-0040-1707864},
number = {21},
pages = {3263--3271},
doi = {10.1055/s-0040-1707864}
}
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MLA
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Smolobochkin, Andrey V., et al. “Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[ d[[1,3]diazepinones.” Synthesis, vol. 52, no. 21, Jun. 2020, pp. 3263-3271. https://doi.org/10.1055/s-0040-1707864.