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

42 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

Access to Document

10.1021/jo00236a007

Cite this

@article{91aaab3c9ef44df2a27c6d7d25d14606,

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

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.",

author = "Alfred Hassner and Amarasekara, {Ananda S.} and Donald Andisik",

year = "1988",

month = jan,

day = "1",

doi = "10.1021/jo00236a007",

language = "אנגלית",

volume = "53",

pages = "27--30",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Intramolecular Azide-Olefin Cycloadditions. A Novel Synthesis of 2,5-Dihydrooxazoles

AU - Hassner, Alfred

AU - Amarasekara, Ananda S.

AU - Andisik, Donald

PY - 1988/1/1

Y1 - 1988/1/1

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0002527831&partnerID=8YFLogxK

U2 - 10.1021/jo00236a007

DO - 10.1021/jo00236a007

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:0002527831

SN - 0022-3263

VL - 53

SP - 27

EP - 30

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this