A convenient synthesis of 3-aryl-1,2,4-oxadiazoles from ethyl acetoacetate and amidoximes under solvent-free conditions

<div class="WordSection1"><p><em>1,2,4-Oxadiazole containing compounds have attracted great attention due to their applications in material chemistry and therapeutics. </em><em>Herein we report a convenient synthesis of 3-aril-[1,2,4-oxadiazol-5yl] propan-2-on...

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Bibliographic Details
Main Authors: Juliana L. L. F. Regueira, João R. de Freitas Filho
Format: Article
Language:English
Published: Universidade Federal de Mato Grosso do Sul 2012-06-01
Series:Orbital: The Electronic Journal of Chemistry
Subjects:
Online Access:http://orbital.ufms.br/index.php/Chemistry/article/view/344
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Summary:<div class="WordSection1"><p><em>1,2,4-Oxadiazole containing compounds have attracted great attention due to their applications in material chemistry and therapeutics. </em><em>Herein we report a convenient synthesis of 3-aril-[1,2,4-oxadiazol-5yl] propan-2-one (<strong>3a-d) </strong>by heating of </em><em>b</em><em>-ceto esters and an amidoximes </em><em>without any solvent and in the absence of base. </em><em>The arylamidoximes (<strong>1a-f</strong>)<strong> </strong>was synthesized in moderate and excellent yields (31- 89%) by reaction of nitrile with hydroxylamine hydrochloride in water at 25ºC. In the general synthetic strategy employed in our study is illustrated in scheme 1. The 3-aril-[1,2,4-oxadiazol-5yl] propan-2-one (<strong>3a-f</strong>)<strong> </strong>were synthesized by treatment of arylamidoxime</em><em> (<strong>1a-f </strong>with </em><em>b</em><em>-ceto esters for 4 hour </em><em>without any solvent and in the absence of base</em><em>. </em><em>The reaction was monitored  by TLC   (thin layer chromatography). </em><em>The heterocycles (<strong>3a-f)</strong></em><em> </em><em>were obtained in moderate and good yields (60-88%). The products were identified using both analytical and spectral data (IR, <sup>1</sup>H and <sup>13</sup>C NMR) and all compounds are in full agreement with the proposed structure.</em></p></div>
ISSN:1984-6428