Synthesis of polysubstituted 3-hydroxypyridines via the revisited hetero-Diels-Alder reaction of 5-alkoxyoxazoles with dienophiles

Chem Commun (Camb). 2012 Jan 18;48(5):768-70. doi: 10.1039/c1cc16562c. Epub 2011 Nov 25.

Abstract

A general and single-step access to polysubstituted 3-hydroxypyridine scaffolds via hetero-Diels-Alder (HDA) reactions between readily prepared 5-ethoxyoxazoles and dienophiles is reported. The HDA reaction, run in the presence of Nd(OTf)(3) at room temperature, was successfully applied to various 5-ethoxyoxazoles showing good functional group tolerance, and led to a straightforward process to obtain useful building-blocks.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Chemistry, Pharmaceutical / methods*
  • Cyclization
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Molecular Structure
  • Neodymium / chemistry
  • Oxazoles / chemistry*
  • Pyridines / chemical synthesis*
  • Stereoisomerism
  • Vitamin B 6 / chemistry

Substances

  • Alkenes
  • Heterocyclic Compounds, 3-Ring
  • Oxazoles
  • Pyridines
  • hydroxypyridines
  • pterocellin A
  • Neodymium
  • Vitamin B 6