title: Synthesis of polysubstituted 3-hydroxypyridines via the revisited hetero-Diels-Alder reaction of 5-alkoxyoxazoles with dienophiles.
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.
authors: Equipe de Chimie Bio-Organique, CNRS UMR 6014-COBRA & FR 3038, IRCOF, rue Lucien Tesnière, 76131 Mont-Saint-Aignan Cedex, France.
authors: Cyrille
authors: C
authors: Sabot
authors: Emilia
authors: E
authors: Oueis
authors: Xavier
authors: X
authors: Brune
authors: Pierre-Yves
authors: PY
authors: Renard
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry; D015394:Molecular Structure; D009354:Neodymium / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D025101:Vitamin B 6 / Q000737:chemistry
chemical_list: D000475:Alkenes; D006575:Heterocyclic Compounds, 3-Ring; D010080:Oxazoles; D011725:Pyridines; C014047:hydroxypyridines; C479813:pterocellin A; D009354:Neodymium; D025101:Vitamin B 6