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

Chem Commun (Camb)

Equipe de Chimie Bio-Organique, CNRS UMR 6014-COBRA & FR 3038, IRCOF, rue Lucien Tesnière, 76131 Mont-Saint-Aignan Cedex, France.

Published: January 2012

AI Article Synopsis

  • The text discusses a method for creating polysubstituted 3-hydroxypyridine compounds using hetero-Diels-Alder (HDA) reactions.
  • The reactions involve 5-ethoxyoxazoles and dienophiles, conducted at room temperature with Nd(OTf)(3) as a catalyst.
  • This approach is highlighted for its efficiency and ability to accommodate different functional groups, providing a simple process to generate valuable chemical building blocks.

Article 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.

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http://dx.doi.org/10.1039/c1cc16562cDOI Listing

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