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Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[ d ][1,3]diazepinones.
- Source :
-
Synthesis . 2020, Vol. 52 Issue 21, p3263-3271. 9p. - Publication Year :
- 2020
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ELECTROPHILIC substitution reactions
*UREA
*BIOACTIVE compounds
Subjects
Details
- Language :
- English
- ISSN :
- 00397881
- Volume :
- 52
- Issue :
- 21
- Database :
- Academic Search Index
- Journal :
- Synthesis
- Publication Type :
- Academic Journal
- Accession number :
- 146514265
- Full Text :
- https://doi.org/10.1055/s-0040-1707864