Regioselective halogenations and subsequent Suzuki-Miyaura coupling onto bicyclic 2-pyridones

J Org Chem. 2010 Feb 5;75(3):972-5. doi: 10.1021/jo902458g.

Abstract

A selective synthesis of 6-bromo-8-iodo dihydro thiazolo ring-fused 2-pyridones is described. These halogenated 2-pyridones are selectively arylated by sequential Suzuki-Miyaura couplings. This approach can advantageously be used to synthesize focused libraries of substituted ring-fused 2-pyridones, a class of compounds with novel antibacterial properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Catalysis
  • Cyclization
  • Halogenation
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pyridones / chemical synthesis*
  • Pyridones / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • Pyridones