BF<sub>3</sub>·OEt<sub>2</sub>-TFAA Mediated Tetra-Functionalization of Amino Acids - Synthesis of Di- and Tri-Substituted 2-Trifluoromethyl Oxazoles in One Pot
Velusamy Karuppusamy, Andivelu Ilangovan
Abstract
A highly efficient, TFAA-BF3·OEt2 mediated multicomponent coupling of amino acid, TFAA, and aromatics provides a broad library of 2-trifluoromethyl equipped 2,5-disubstituted/2,4,5-trisubstituted oxazoles or N-(trifluoroacetyl)-β-aminoalkyl ketones. This amino acid tetra-functionalization approach involves amidation (C–N), anhydride (C–O), Friedel–Crafts acylation (C–C), and Robinson–Gabriel annulation (C–O) followed by dehydrative aromatization. This reaction takes place under operationally simple, mild, and metal-free conditions using readily available amino acids and aromatic compounds.
Topics & Concepts
ChemistryTetraTrifluoromethylAnnulationAcylationSurface modificationAromatizationFriedel–Crafts reactionOrganic chemistryMedicinal chemistryCombinatorial chemistryCatalysisAlkylPhysical chemistryFluorine in Organic ChemistrySynthesis and Reactions of Organic CompoundsSynthesis and Biological Evaluation