Synthesis of 2,5-Dialkyl-1,3,4-oxadiazoles Bearing Carboxymethylamino Groups
A series of new symmetrical 2,5-dialkyl-1,3,4-oxadiazoles containing substituted alkyl groups at the terminal positions with substituents, such as bromine, isopropyloxycarbonylmethylamino, and carboxymethylamino, were successfully synthesized. The developed multistep method employed commercially ava...
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| Format: | Article |
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MDPI AG
2022-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/22/7687 |
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| author | Marcin Łuczyński Kornelia Kubiesa Agnieszka Kudelko |
| author_facet | Marcin Łuczyński Kornelia Kubiesa Agnieszka Kudelko |
| author_sort | Marcin Łuczyński |
| collection | DOAJ |
| description | A series of new symmetrical 2,5-dialkyl-1,3,4-oxadiazoles containing substituted alkyl groups at the terminal positions with substituents, such as bromine, isopropyloxycarbonylmethylamino, and carboxymethylamino, were successfully synthesized. The developed multistep method employed commercially available acid chlorides differing in alkyl chain length and terminal substituent, hydrazine hydrate, and phosphorus oxychloride. The intermediate bromine-containing 2,5-dialkyl-1,3,4-oxadiazoles were easily substituted with diisopropyl iminodiacetate, followed by hydrolysis in aqueous methanol solution giving the corresponding 1,3,4-oxadiazoles bearing carboxymethylamino substituents. The structure of all products was confirmed by conventional spectroscopic methods including <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. |
| first_indexed | 2024-03-09T18:08:14Z |
| format | Article |
| id | doaj.art-b62374a5bc2f4fb69d4ea9bb54ae5e28 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T18:08:14Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b62374a5bc2f4fb69d4ea9bb54ae5e282023-11-24T09:19:25ZengMDPI AGMolecules1420-30492022-11-012722768710.3390/molecules27227687Synthesis of 2,5-Dialkyl-1,3,4-oxadiazoles Bearing Carboxymethylamino GroupsMarcin Łuczyński0Kornelia Kubiesa1Agnieszka Kudelko2Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, PolandDepartment of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, PolandDepartment of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, PolandA series of new symmetrical 2,5-dialkyl-1,3,4-oxadiazoles containing substituted alkyl groups at the terminal positions with substituents, such as bromine, isopropyloxycarbonylmethylamino, and carboxymethylamino, were successfully synthesized. The developed multistep method employed commercially available acid chlorides differing in alkyl chain length and terminal substituent, hydrazine hydrate, and phosphorus oxychloride. The intermediate bromine-containing 2,5-dialkyl-1,3,4-oxadiazoles were easily substituted with diisopropyl iminodiacetate, followed by hydrolysis in aqueous methanol solution giving the corresponding 1,3,4-oxadiazoles bearing carboxymethylamino substituents. The structure of all products was confirmed by conventional spectroscopic methods including <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS.https://www.mdpi.com/1420-3049/27/22/76871,3,4-oxadiazolesorganic ligandsheterocyclessubstitutiondiisopropyl iminodiacetate |
| spellingShingle | Marcin Łuczyński Kornelia Kubiesa Agnieszka Kudelko Synthesis of 2,5-Dialkyl-1,3,4-oxadiazoles Bearing Carboxymethylamino Groups Molecules 1,3,4-oxadiazoles organic ligands heterocycles substitution diisopropyl iminodiacetate |
| title | Synthesis of 2,5-Dialkyl-1,3,4-oxadiazoles Bearing Carboxymethylamino Groups |
| title_full | Synthesis of 2,5-Dialkyl-1,3,4-oxadiazoles Bearing Carboxymethylamino Groups |
| title_fullStr | Synthesis of 2,5-Dialkyl-1,3,4-oxadiazoles Bearing Carboxymethylamino Groups |
| title_full_unstemmed | Synthesis of 2,5-Dialkyl-1,3,4-oxadiazoles Bearing Carboxymethylamino Groups |
| title_short | Synthesis of 2,5-Dialkyl-1,3,4-oxadiazoles Bearing Carboxymethylamino Groups |
| title_sort | synthesis of 2 5 dialkyl 1 3 4 oxadiazoles bearing carboxymethylamino groups |
| topic | 1,3,4-oxadiazoles organic ligands heterocycles substitution diisopropyl iminodiacetate |
| url | https://www.mdpi.com/1420-3049/27/22/7687 |
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