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

Alfred Hassner, Ananda S. Amarasekara, Donald Andisik

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)27-30
Number of pages4
JournalJournal of Organic Chemistry
Volume53
Issue number1
DOIs
StatePublished - 1 Jan 1988

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