Hydantoin-bridged medium ring scaffolds by migratory insertion of urea-tethered nitrile anions into aromatic C-N bonds

Makenzie J. Millward, Emily Ellis, John W. Ward, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

2 Citations (Scopus)
24 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)2091-2096
Number of pages6
JournalChemical Science
Volume12
Issue number6
Early online date14 Dec 2020
DOIs
Publication statusPublished - 14 Feb 2021

Structured keywords

  • BCS and TECS CDTs

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