1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes

1-Azetines as thiocyanate equivalents

Karl Hemming, Musharraf N. Khan, Paul A. O'Gorman, Arnaud Pitard

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

1,3-Dipolar cycloaddition of nitrile oxides to 4-aryl-2-alkylthio-1- azetines gave a series of oxadiazabicyclo[3.2.0]heptenes as single diastereoisomers. Heating these cycloadducts in toluene resulted in an overall [2+2]-cycloreversion to give 5-alkylthio-3-aryl-1,2,4-oxadiazoles. In this process, the 1-azetine behaves as a thiocyanate equivalent. When the nitrile oxide substituent was 2-azidobenzene, the azide could be converted into a 1,2,3-triazole giving a (1,2,4-oxadiazolo)-(1,2,3-triazolo)-1,2-disubstituted benzene. 1,2,4-Oxadiazoles are sought after in medicinal chemistry and materials sciences.

Original languageEnglish
Pages (from-to)1279-1284
Number of pages6
JournalTetrahedron
Volume69
Issue number4
Early online date7 Dec 2012
DOIs
Publication statusPublished - 28 Jan 2013

Fingerprint

Azetines
Oxadiazoles
Nitriles
Oxides
Triazoles
Azides
Cycloaddition
Pharmaceutical Chemistry
Cycloaddition Reaction
Toluene
Materials science
Benzene
Heating
thiocyanate

Cite this

Hemming, Karl ; Khan, Musharraf N. ; O'Gorman, Paul A. ; Pitard, Arnaud. / 1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes : 1-Azetines as thiocyanate equivalents. In: Tetrahedron. 2013 ; Vol. 69, No. 4. pp. 1279-1284.
@article{7e9a6a34c97042f4825587e1bf2b8dcc,
title = "1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes: 1-Azetines as thiocyanate equivalents",
abstract = "1,3-Dipolar cycloaddition of nitrile oxides to 4-aryl-2-alkylthio-1- azetines gave a series of oxadiazabicyclo[3.2.0]heptenes as single diastereoisomers. Heating these cycloadducts in toluene resulted in an overall [2+2]-cycloreversion to give 5-alkylthio-3-aryl-1,2,4-oxadiazoles. In this process, the 1-azetine behaves as a thiocyanate equivalent. When the nitrile oxide substituent was 2-azidobenzene, the azide could be converted into a 1,2,3-triazole giving a (1,2,4-oxadiazolo)-(1,2,3-triazolo)-1,2-disubstituted benzene. 1,2,4-Oxadiazoles are sought after in medicinal chemistry and materials sciences.",
keywords = "1,2,3-Triazole, 1,2,4-Oxadiazole, Azetine, Azide, Cycloreversion, Nitrile oxide",
author = "Karl Hemming and Khan, {Musharraf N.} and O'Gorman, {Paul A.} and Arnaud Pitard",
year = "2013",
month = "1",
day = "28",
doi = "10.1016/j.tet.2012.12.007",
language = "English",
volume = "69",
pages = "1279--1284",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "4",

}

1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes : 1-Azetines as thiocyanate equivalents. / Hemming, Karl; Khan, Musharraf N.; O'Gorman, Paul A.; Pitard, Arnaud.

In: Tetrahedron, Vol. 69, No. 4, 28.01.2013, p. 1279-1284.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes

T2 - 1-Azetines as thiocyanate equivalents

AU - Hemming, Karl

AU - Khan, Musharraf N.

AU - O'Gorman, Paul A.

AU - Pitard, Arnaud

PY - 2013/1/28

Y1 - 2013/1/28

N2 - 1,3-Dipolar cycloaddition of nitrile oxides to 4-aryl-2-alkylthio-1- azetines gave a series of oxadiazabicyclo[3.2.0]heptenes as single diastereoisomers. Heating these cycloadducts in toluene resulted in an overall [2+2]-cycloreversion to give 5-alkylthio-3-aryl-1,2,4-oxadiazoles. In this process, the 1-azetine behaves as a thiocyanate equivalent. When the nitrile oxide substituent was 2-azidobenzene, the azide could be converted into a 1,2,3-triazole giving a (1,2,4-oxadiazolo)-(1,2,3-triazolo)-1,2-disubstituted benzene. 1,2,4-Oxadiazoles are sought after in medicinal chemistry and materials sciences.

AB - 1,3-Dipolar cycloaddition of nitrile oxides to 4-aryl-2-alkylthio-1- azetines gave a series of oxadiazabicyclo[3.2.0]heptenes as single diastereoisomers. Heating these cycloadducts in toluene resulted in an overall [2+2]-cycloreversion to give 5-alkylthio-3-aryl-1,2,4-oxadiazoles. In this process, the 1-azetine behaves as a thiocyanate equivalent. When the nitrile oxide substituent was 2-azidobenzene, the azide could be converted into a 1,2,3-triazole giving a (1,2,4-oxadiazolo)-(1,2,3-triazolo)-1,2-disubstituted benzene. 1,2,4-Oxadiazoles are sought after in medicinal chemistry and materials sciences.

KW - 1,2,3-Triazole

KW - 1,2,4-Oxadiazole

KW - Azetine

KW - Azide

KW - Cycloreversion

KW - Nitrile oxide

UR - http://www.scopus.com/inward/record.url?scp=84871971349&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.12.007

DO - 10.1016/j.tet.2012.12.007

M3 - Article

VL - 69

SP - 1279

EP - 1284

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 4

ER -