Abstract
We report the synthesis of 6-arylthio-substituted-N-alkenyl 2-pyridones by ring opening of bicyclic thiazolino-2-pyridones with arynes. Varied functionalization was used to investigate scope and substituent influences on reactivity. Selected conditions favor thioether ring opening over [4 + 2] cycloaddition and an unusual aryne incorporating ring expansion. Deuterium labeling was used to clarify observed reactivity. Using the knowledge, we produced drug-like molecules with complex substitution patterns and show how thioether ring opening can be used on scaffolds with competing reactivities.
Original language | English |
---|---|
Pages (from-to) | 6946-6950 |
Number of pages | 5 |
Journal | Organic Letters |
Volume | 21 |
Issue number | 17 |
Early online date | 16 Aug 2019 |
DOIs | |
Publication status | Published - 16 Sept 2019 |
Keywords
- Peptides and proteins
- Cyclization
- Substituents
- Ring opening reactions
- Reactivity
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry