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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| Format: | Article |
| Language: | English |
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Universidade Federal de Mato Grosso do Sul
2012-06-01
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| Series: | Orbital: The Electronic Journal of Chemistry |
| Subjects: | |
| Online Access: | http://orbital.ufms.br/index.php/Chemistry/article/view/344 |
| _version_ | 1818976847361212416 |
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| author | Juliana L. L. F. Regueira João R. de Freitas Filho |
| author_facet | Juliana L. L. F. Regueira João R. de Freitas Filho |
| author_sort | Juliana L. L. F. Regueira |
| collection | DOAJ |
| description | <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> |
| first_indexed | 2024-12-20T16:18:21Z |
| format | Article |
| id | doaj.art-708028154a3a419481dd2dcb932995f9 |
| institution | Directory Open Access Journal |
| issn | 1984-6428 |
| language | English |
| last_indexed | 2024-12-20T16:18:21Z |
| publishDate | 2012-06-01 |
| publisher | Universidade Federal de Mato Grosso do Sul |
| record_format | Article |
| series | Orbital: The Electronic Journal of Chemistry |
| spelling | doaj.art-708028154a3a419481dd2dcb932995f92022-12-21T19:33:43ZengUniversidade Federal de Mato Grosso do SulOrbital: The Electronic Journal of Chemistry1984-64282012-06-0141131410.17807/orbital.v4i1.344114A convenient synthesis of 3-aryl-1,2,4-oxadiazoles from ethyl acetoacetate and amidoximes under solvent-free conditionsJuliana L. L. F. Regueira0João R. de Freitas Filho1Departamento de Ciências Moleculares, Universidade Federal Rural de PernambucoDepartamento de Ciências Moleculares, Universidade Federal Rural de Pernambuco<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>http://orbital.ufms.br/index.php/Chemistry/article/view/344amidoximes1,2,4-oxadiazolessolvent-free |
| spellingShingle | Juliana L. L. F. Regueira João R. de Freitas Filho A convenient synthesis of 3-aryl-1,2,4-oxadiazoles from ethyl acetoacetate and amidoximes under solvent-free conditions Orbital: The Electronic Journal of Chemistry amidoximes 1,2,4-oxadiazoles solvent-free |
| title | A convenient synthesis of 3-aryl-1,2,4-oxadiazoles from ethyl acetoacetate and amidoximes under solvent-free conditions |
| title_full | A convenient synthesis of 3-aryl-1,2,4-oxadiazoles from ethyl acetoacetate and amidoximes under solvent-free conditions |
| title_fullStr | A convenient synthesis of 3-aryl-1,2,4-oxadiazoles from ethyl acetoacetate and amidoximes under solvent-free conditions |
| title_full_unstemmed | A convenient synthesis of 3-aryl-1,2,4-oxadiazoles from ethyl acetoacetate and amidoximes under solvent-free conditions |
| title_short | A convenient synthesis of 3-aryl-1,2,4-oxadiazoles from ethyl acetoacetate and amidoximes under solvent-free conditions |
| title_sort | convenient synthesis of 3 aryl 1 2 4 oxadiazoles from ethyl acetoacetate and amidoximes under solvent free conditions |
| topic | amidoximes 1,2,4-oxadiazoles solvent-free |
| url | http://orbital.ufms.br/index.php/Chemistry/article/view/344 |
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