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

Alfred Hassner; Ananda S. Amarasekara; Donald Andisik

doi:10.1021/jo00236a007

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

Alfred Hassner, Ananda S. Amarasekara, Donald Andisik

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

43 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 language	English
Pages (from-to)	27-30
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	53
Issue number	1
DOIs	https://doi.org/10.1021/jo00236a007
State	Published - 1 Jan 1988

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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.",

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AB - 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.

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

Abstract

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