Intramolecular Azide-Olefin Cycloadditions. A Novel Synthesis of 2,5-Dihydrooxazoles

Article abstract of DOI:10.1021/jo00236a007

A facile synthetic route from aldehydes to allyl α-azidoalkyl ether 2 is described.Thermolysis of 2 proceeds by intramolecular azide-olefin cycloaddition via triazolines and provides a novel synthesis of 2,5-dihydrooxazoles 6.The use of silica gel in the chemoselective conversion of the intermediate triazolines to bicyclic aziridines 7 is described.