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Application of N-Acylbenzotriazoles in the Synthesis of 5-Substituted 2-Ethoxy-1,3,4-oxadiazoles as Building Blocks toward 3,5-Disubstituted 1,3,4-Oxadiazol-2(3H)-ones.

Authors :
Wet-Osot S
Phakhodee W
Pattarawarapan M
Source :
The Journal of organic chemistry [J Org Chem] 2017 Sep 15; Vol. 82 (18), pp. 9923-9929. Date of Electronic Publication: 2017 Sep 01.
Publication Year :
2017

Abstract

5-Substituted-2-ethoxy-1,3,4-oxadiazoles were conveniently prepared through a one-pot sequential N-acylation/dehydrative cyclization between ethyl carbazate and N-acylbenzotriazoles in the presence of Ph <subscript>3</subscript> P-I <subscript>2</subscript> as a dehydrating agent. Subsequent treatment with a stoichiometric amount of alkyl halides (X = Cl, Br, I) enables a rapid access to a variety of 3,5-disubstituted 1,3,4-oxadiazol-2(3H)-ones in good to excellent yields.

Details

Language :
English
ISSN :
1520-6904
Volume :
82
Issue :
18
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
28862855
Full Text :
https://doi.org/10.1021/acs.joc.7b01863