Precious-Metal-Free Heteroarylation of Azlactones: Direct Synthesis of α-Pyridyl, α-Substituted Amino Acid Derivatives.
A one-pot, three-component synthesis of α-pyridyl, α-substituted amino acid derivatives is described. The key transformation is a direct, precious-metal-free heteroarylation of readily available, amino acid derived azlactones with electrophilically activated pyridine N-oxides. The resulting intermediates can be used directly as efficient acylating agents for a range of nucleophiles, leading to the heteroarylated amino acid derivatives in a single vessel.
School of Chemistry and Institute of Process Research and Development, University of Leeds , Leeds, LS2 9JT, U.K.
Tarn C
TC
Johnson
School of Chemistry and Institute of Process Research and Development, University of Leeds , Leeds, LS2 9JT, U.K.
Stephen P
SP
Marsden
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D005021:Ethylamines / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D000432:Methanol / Q000737:chemistry; D010087:Oxides / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis*; D012997:Solvents / Q000737:chemistry
D000596:Amino Acids; D005021:Ethylamines; D007783:Lactones; D010087:Oxides; D011725:Pyridines; D012997:Solvents; C016162:triethylamine; D000432:Methanol