Microwave-Assisted Synthesis of Unsymmetrical 5-Phenyl-1,3,4-oxadiazoles Containing Bis(carboxymethyl)amino Group
New derivatives of 5-phenyl-1,3,4-oxadiazole substituted at position 2 with (bromomethyl)phenyl or bromoalkyl groups were obtained via microwave-assisted cyclodehydration of unsymmetrical <i>N,N′</i>-diacylhydrazines. Then, bromine-containing oxadiazoles were substituted with diisopropyl...
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| Format: | Article |
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MDPI AG
2023-11-01
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| Series: | Applied Sciences |
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| Online Access: | https://www.mdpi.com/2076-3417/13/22/12427 |
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| author | Marcin Łuczyński Agnieszka Kudelko |
| author_facet | Marcin Łuczyński Agnieszka Kudelko |
| author_sort | Marcin Łuczyński |
| collection | DOAJ |
| description | New derivatives of 5-phenyl-1,3,4-oxadiazole substituted at position 2 with (bromomethyl)phenyl or bromoalkyl groups were obtained via microwave-assisted cyclodehydration of unsymmetrical <i>N,N′</i>-diacylhydrazines. Then, bromine-containing oxadiazoles were substituted with diisopropyl iminodiacetate, yielding the corresponding ester derivatives, which were subsequently hydrolyzed in an aqueous methanol solution. The cleavage of the ester group resulted in the formation of the appropriate 5-phenyl-1,3,4-oxadiazoles bearing bis(carboxymethyl)amino groups in satisfactory yields. The structures of all products were confirmed by typical spectroscopic methods including 1H and 13C NMR, and HRMS. |
| first_indexed | 2024-03-09T17:02:54Z |
| format | Article |
| id | doaj.art-cc09bb37ae64430da72058d87a411fe3 |
| institution | Directory Open Access Journal |
| issn | 2076-3417 |
| language | English |
| last_indexed | 2024-03-09T17:02:54Z |
| publishDate | 2023-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Applied Sciences |
| spelling | doaj.art-cc09bb37ae64430da72058d87a411fe32023-11-24T14:27:43ZengMDPI AGApplied Sciences2076-34172023-11-0113221242710.3390/app132212427Microwave-Assisted Synthesis of Unsymmetrical 5-Phenyl-1,3,4-oxadiazoles Containing Bis(carboxymethyl)amino GroupMarcin Łuczyński0Agnieszka Kudelko1Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44100 Gliwice, PolandDepartment of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44100 Gliwice, PolandNew derivatives of 5-phenyl-1,3,4-oxadiazole substituted at position 2 with (bromomethyl)phenyl or bromoalkyl groups were obtained via microwave-assisted cyclodehydration of unsymmetrical <i>N,N′</i>-diacylhydrazines. Then, bromine-containing oxadiazoles were substituted with diisopropyl iminodiacetate, yielding the corresponding ester derivatives, which were subsequently hydrolyzed in an aqueous methanol solution. The cleavage of the ester group resulted in the formation of the appropriate 5-phenyl-1,3,4-oxadiazoles bearing bis(carboxymethyl)amino groups in satisfactory yields. The structures of all products were confirmed by typical spectroscopic methods including 1H and 13C NMR, and HRMS.https://www.mdpi.com/2076-3417/13/22/12427<i>N,N′</i>-diacylhydrazinescyclizationmicrowaves1,3,4-oxadiazolessubstitutiondiisopropyl iminodiacetate |
| spellingShingle | Marcin Łuczyński Agnieszka Kudelko Microwave-Assisted Synthesis of Unsymmetrical 5-Phenyl-1,3,4-oxadiazoles Containing Bis(carboxymethyl)amino Group Applied Sciences <i>N,N′</i>-diacylhydrazines cyclization microwaves 1,3,4-oxadiazoles substitution diisopropyl iminodiacetate |
| title | Microwave-Assisted Synthesis of Unsymmetrical 5-Phenyl-1,3,4-oxadiazoles Containing Bis(carboxymethyl)amino Group |
| title_full | Microwave-Assisted Synthesis of Unsymmetrical 5-Phenyl-1,3,4-oxadiazoles Containing Bis(carboxymethyl)amino Group |
| title_fullStr | Microwave-Assisted Synthesis of Unsymmetrical 5-Phenyl-1,3,4-oxadiazoles Containing Bis(carboxymethyl)amino Group |
| title_full_unstemmed | Microwave-Assisted Synthesis of Unsymmetrical 5-Phenyl-1,3,4-oxadiazoles Containing Bis(carboxymethyl)amino Group |
| title_short | Microwave-Assisted Synthesis of Unsymmetrical 5-Phenyl-1,3,4-oxadiazoles Containing Bis(carboxymethyl)amino Group |
| title_sort | microwave assisted synthesis of unsymmetrical 5 phenyl 1 3 4 oxadiazoles containing bis carboxymethyl amino group |
| topic | <i>N,N′</i>-diacylhydrazines cyclization microwaves 1,3,4-oxadiazoles substitution diisopropyl iminodiacetate |
| url | https://www.mdpi.com/2076-3417/13/22/12427 |
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