Journal
TETRAHEDRON
Volume 66, Issue 4, Pages 986-994Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.11.079
Keywords
Ionic liquid; Liquid phase; 1,2,4-oxadiazole; Bioisostere; O-acylamidoxime; Amidoxime
Categories
Funding
- Ministere de la Recherche et de l'Enseignement Superieur
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New 3,5-disubstituted 1,2,4-oxadiazoles were synthesized in five steps by ionic liquid-phase organic synthesis (IoLiPOS) methodology. The strategy involved the preparation of amidoxime from the ionic liquid-phase bound arylnitrile. Addition of various carboxylic acid to the amidoxime produced the expected 3,5-disubstituted 1,2,4-oxadiazoles via the stable O-acyl amidoxime intermediate grafted on the ionic liquid-phase. The 1,2,4-oxadiazoles were easily cleaved by tran sesterification under mild reaction conditions in high purity with good overall yields. The structures of the intermediates in each step were verified by routine spectroscopic analysis (H-1, C-13 NMR, and HRMS). (C) 2009 Elsevier Ltd. All rights reserved.
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