Synthesis of 3,5-disubstituted 1,2,4-oxadiazoles using ionic liquid-phase organic synthesis (IoLiPOS) methodology |
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| Authors: | Laetitia Duchet Daniel Carrié Jean Jacques Vanden Eynde |
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| Institution: | a Université de Rennes 1, Laboratoire Sciences Chimiques de Rennes, UMR CNRS 6226, Groupe Ingénierie Chimique & Molécules pour le Vivant (ICMV), Bât. 10A, Campus de Beaulieu, Avenue du Général Leclerc, CS 74205, 35042 Rennes Cedex, France
b Université de Mons, Département de Chimie Organique, 20 Place du Parc, 7000 Mons, Belgium |
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| Abstract: | 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 transesterification 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 (1H, 13C NMR, and HRMS). |
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| Keywords: | Ionic liquid Liquid phase 1 2 4-Oxadiazole Bioisostere O-acylamidoxime Amidoxime |
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