Development of a diversity-oriented approach to oxazole-5-amide libraries.
A highly versatile route to oxazole-5-amides is presented. Conversion of readily accessible oxazole-5-trifluoroacetamides into their Boc-protected 5-aminooxazole derivatives provides intermediates amenable to parallel amide synthesis utilizing a reliable, one-pot, acylation-deprotection procedure. During preparation of the N-Boc compounds from trifluoroacetamides, a competing intramolecular rearrangement giving rise to novel N-(oxazol-5-yl)-2,2,2-trifluoroacetimidates was identified, the extent of which is primarily determined by the choice of reaction conditions.
Thompson
Mark J
MJ
Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK.
Adams
Harry
H
Chen
Beining
B
D000081:Acetamides; D000215:Acylation; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D005463:Fluoroacetates; D009682:Magnetic Resonance Spectroscopy; D010080:Oxazoles / Q000737:chemistry*; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry; D014269:Trifluoroacetic Acid / Q000737:chemistry
D000081:Acetamides; D000577:Amides; D005463:Fluoroacetates; D010080:Oxazoles; D054852:Small Molecule Libraries; C030688:trifluoroacetamide; D014269:Trifluoroacetic Acid