Mossetti, RiccardoPirali, TraceyTron, Gian CesareZhu, Jieping2010-11-252010-11-252010-11-25201010.1021/ol902894phttps://infoscience.epfl.ch/handle/20.500.14299/58592Acyl chlorides R1COCl [R1 = Et, n-pentyl, PhCH2CH2, 2-cyclopentylethyl, (S)-PhCHEt] efficiently reacted with alpha -isocyanoacetamides R2R3NCOCH(NC)R4 (R2 = H, R3 = n-Bu, PhCH2, HC==CCH2; R2 = Me, R3 = HC==CCH2, PhCH2; R2R3N = 4-morpholinyl; R4 = H, Me, PhCH2) in dichloromethane in the presence of triethylamine to give 2-acyl-5-aminooxazoles I. Subsequent acid hydrolysis of the 5-aminooxazole moiety leads to alpha -ketoamides II in good overall yields. [on SciFinder (R)]Acid halides Role: RCT (Reactant)RACT (Reactant or reagent) (acid chlorides; efficient synthesis of alpha -ketoamides via cyclocondensation of acyl chlorides with alpha -isocyano amides followed by hydrolysis/ring opening of 2-acyl-5-aminooxazoles); Heterocyclization (efficient synthesis of alpha -ketoamides via cyclocondensation of acyl chlorides with alpha -isocyano amides followed by hydrolysis/ring opening of 2-acyl-5-aminooxazoles); Isocyanides Role: RCT (Reactant)RACT (Reactant or reagent) (efficient synthesis of alpha -ketoamides via cyclocondensation of acyl chlorides with alpha -isocyano amides followed by hydrolysis/ring opening of 2-acyl-5-aminooxazoles); Ring opening (hydrolytic; efficient synthesis of alpha -ketoamides via cyclocondensation of acyl chlorides with alpha -isocyano amides followed by hydrolysis/ring opening of 2-acyl-5-aminooxazoles); Amides Role: SPN (Synthetic preparation)PREP (Preparation) (oxo; efficient synthesis of alpha -ketoamides via cyclocondensation of acyl chlorides with alpha -isocyano amides followed by hydrolysis/ring opening of 2-acyl-5-aminooxazoles); Hydrolysis (ring opening; efficient synthesis of alpha -ketoamides via cyclocondensation of acyl chlorides with alpha -isocyano amides followed by hydrolysis/ring opening of 2-acyl-5-aminooxazoles)amide keto prepn; oxazole acyl amino prepn hydrolysis ring opening; isonitrile amide cyclocondensation acyl chlorideEfficient Synthesis of alpha -Ketoamides via 2-Acyl-5-aminooxazoles by Reacting Acyl Chlorides and alpha -Isocyanoacetamidestext::journal::journal article::research article