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Synthesis 2020; 52(21): 3263-3271
DOI: 10.1055/s-0040-1707864
DOI: 10.1055/s-0040-1707864
special topic
Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones
The synthetic part of this work was made with financial support from the government assignment for the Federal Research Center, Kazan Scientific Center of the Russian Academy of Sciences. The X-ray studies were supported by Russian Science Foundation (Grant No. 19-13-00238). The X-ray measurements were performed using shared experimental facilities supported by an Institute of General and Inorganic Chemistry, Russian Academy of Sciences state assignment.Further Information
Publication History
Received: 26 March 2020
Accepted after revision: 15 May 2020
Publication Date:
10 June 2020 (online)
Published as part of the Special Topic Recent Advances in Amide Bond Formation
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.
Key words
(2,2-dialkoxyethyl)ureas - imidazolidin-2-ones - 1,3-benzodiazepin-2-ones - cyclization - cyclic ureasSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707864.
- Supporting Information
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