Millward, Makenzie J, Ellis, Emily, Ward, John W 
ORCID: 0000-0001-7186-6416 and Clayden, Jonathan
(2021)
Hydantoin-bridged medium ring scaffolds by migratory insertion of urea-tethered nitrile anions into aromatic C-N bonds.
CHEMICAL SCIENCE, 12 (6).
pp. 2091-2096.
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Hydantoin-bridged medium ring scaffolds by migratory insertion of urea-tethered nitrile anions into aromatic C-N bonds.pdf - Published version Download (2MB) | Preview |
Abstract
Bicyclic or tricyclic nitrogen-containing heterocyclic scaffolds were constructed rapidly by intramolecular nucleophilic aromatic substitution of metallated nitriles tethered by a urea linkage to a series of electronically unactivated heterocyclic precursors. The substitution reaction constitutes a ring expansion, enabled by the conformationally constrained tether between the nitrile and the heterocycle. Attack of the metallated urea leaving group on the nitrile generates a hydantoin that bridges the polycyclic products. X-ray crystallography reveals ring-dependant strain within the hydantoin.
| Item Type: | Article |
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| Divisions: | Faculty of Science and Engineering > School of Physical Sciences |
| Depositing User: | Symplectic Admin |
| Date Deposited: | 06 Sep 2021 14:42 |
| Last Modified: | 18 Jan 2023 21:29 |
| DOI: | 10.1039/d0sc06188c |
| Open Access URL: | https://pubs.rsc.org/en/content/articlelanding/202... |
| Related URLs: | |
| URI: | https://livrepository.liverpool.ac.uk/id/eprint/3136108 |
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