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- Title
Medium-Ring Nitrogen Heterocycles through Migratory Ring Expansion of Metalated Ureas.
- Authors
Hall, Jessica E.; Matlock, Johnathan V.; Ward, John W.; Gray, Katharine V.; Clayden, Jonathan
- Abstract
Simple benzo-fused nitrogen heterocycles (indolines, tetrahydroquinolines, and their homologues) undergo migratory ring expansion through deprotonation of their benzylic urea derivatives with lithium diisopropylamide (LDA) in the presence of N,N′-dimethylpropylideneurea (DMPU). The products of the reactions are benzodiazepines, benzodiazocines, and their homologues, with ring sizes of 8-12. The reactions tolerate a range of substituent patterns and types, and may exhibit enantiospecificity or diastereoselectivity. Considerable complexity is rapidly generated in an efficient synthesis of these otherwise difficult-to-obtain medium-ring nitrogen heterocycles.
- Subjects
NITROGEN compound synthesis; PROTON transfer reactions; METALATION; HETEROCYCLIC compounds synthesis; INTRAMOLECULAR proton transfer reactions; CHARGE transfer; CHEMICAL reactions
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 37, p11153
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201605714