Oxazoline synthesis from hydroxyamides by resin capture and ring-forming release.
Polymer-bound tosyl chloride was used to capture hydroxyamides (prepared from amino alcohols and acid chlorides) from the reaction mixtures in which they were formed. The resulting support-bound amide/ sulfonates undergo ring-forming cleavage from the polymer on treatment with weak base, forming oxazolines and oxazines in generally good yield and high purity. Low temperature is required in the polymer-loading step to slow the cleavage process and achieve high efficiency in the execution of the method.
Pirrung
M C
MC
Department of Chemistry, Levine Science Research Center, Duke University, Durham North Carolina 27708-0317, USA.
Tumey
L N
LN
D000577:Amides / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D010080:Oxazoles / Q000138:chemical synthesis*; D012116:Resins, Plant
D000577:Amides; D010080:Oxazoles; D012116:Resins, Plant