Synthesis of Densely Functionalized N-Alkenyl 2-Pyridones via Benzyne-Induced Ring Opening of Thiazolino-Fused 2-Pyridones

Pardeep Singh, Andrew G. Cairns, Dan E. Adolfsson, Jörgen Ådén, Uwe H. Sauer, Fredrik Almqvist (Lead / Corresponding author)

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

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 languageEnglish
Pages (from-to)6946-6950
Number of pages5
JournalOrganic Letters
Volume21
Issue number17
Early online date16 Aug 2019
DOIs
Publication statusPublished - 16 Sep 2019

Keywords

  • Peptides and proteins
  • Cyclization
  • Substituents
  • Ring opening reactions
  • Reactivity

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