PERSPEKTIVNYI PODKHOD K SINTEZU 2,5-DIZAMESHCHENNYKH 1,3,4 OKSADIAZOLOV
Abstract and keywords
Abstract:
Razrabotan effektivnyy metod sinteza 2,5-dizameschennyh 1,3,4 oksadiazolov, vklyuchayuschiy poluchenie ishodnyh gidrazidov aromaticheskih kislot, ih prevraschenie v N-acilgidrazony i posleduyuschuyu okislitel'nuyu ciklizaciyu s ispol'zovaniem sistemy I2/K2CO3 v srede DMSO. Pokazano, chto predlozhennyy podhod obespechivaet vysokie vyhody celevyh 1,3,4-oksadiazolov (do 78%).

Keywords:
1,3,4-oksadiazoly; ciklizaciya, tverdofaznyy metod
References

1. Li Z., Li W., Keum C., Archer E., Zhao B., Slawin A.M.Z., Huang W., Gather M.C., Samuel I.D.W., Zysman Colman E. 1,3,4-Oxadiazole-based deep blue thermally activated delayed fluorescence emitters for organic light-emitting diodes. J. Phys. Chem. C, 2019,123, 24772–24785. DOI:https://doi.org/10.1021/acs.jpcc.9b08479

2. Ye H., Wu H., Chen L., Ma S., Zhou K., Yan G., Shen J., Chen D., Su S.-J. Synthesis, properties, calculations and applications of small molecular host materials containing oxadiazole units with different nitrogen and oxygen atom orientations for solution-processable blue phosphorescent OLEDs. Electron. Mater. Lett., 2018, 14, 89–100. DOI:https://doi.org/10.1007/s13391-018-0011-8

3. Yusifova Yu.R., Firstova A.A. 1,3,4-Oksadiazoly: strategii sinteza i primenenie. Ot himii k tehnologii shag za shagom, 2025, 6(2), 8- 33. URL: https://chemintech.ru/ru/nauka/issue/6013/view DOI: https://doi.org/10.52957/2782-1900-2025-6-2-8-33

4. Voronin A.A., Fedyanin I.V., Chupakov A.M., Pivkina A.N., Muravyev N.V., Strelenko Y.A., Klenov M.S., Lumpert D.B., Tartakovsky V.A. 4H-[1,2,3]Triazolo[4,5-c][1,2,5]oxadiazole 5-oxide and Its Salts: Promising Multipurpose Energetic Materials. ACS Appl. Energy Mater., 2020, 3(9), 9401–9407. DOI:https://doi.org/10.1021/acsaem.0c01769

5. Kushwaha D., Tiwari V.K. Click Inspired Synthesis of 1,2,3-Triazole-linked 1,3,4-Oxadiazole Glycoconjugates. J. Heterocycl. Chem., 2017, 54(4), 2454–2462. DOI:https://doi.org/10.1002/jhet.2845

6. Alkhaldi A.A.M., Abdelgawad M.A., Youssif B.G.M., El-gendy A.O., De Koning H.P. Synthesis, antimicrobial activities and GAPDH docking of novel 1,2,3-triazole derivatives. Trop. J. Pharm. Res., 2019, 18(5), 1101–1108. DOI:https://doi.org/10.4314/tjpr.v18i5.27

7. Frohlichova Z., Tomascikova J., Imrich I., Kristian P., Danihel I., Bohm S., Sabolova D. Synthesis and properties of novel biologically interesting polycyclic 1,3,4-oxadiazoles containing acridine/acridone moieties. Heterocycles, 2009, 77(2), 1019–1035. DOI:https://doi.org/10.1002/chin.200928133

8. Beal D.M., Bryans J.S., Johnson P.S., Newman J., Pasquinet C., Peakman T.M., Ryckmans T., Wheeler S. Preparation of triazolobenzodiazepine derivatives as Vasopressin V1a antagonists. Tetrahedron Lett., 2011, 52(45), 5913–5917. DOI:https://doi.org/10.1016/j.tetlet.2011.08.011

9. Karthikeyan M.S., Prasad D.J., Mahalinga M., Holla B.S. Antimicrobial studies of 2,5-dichloro-5-fluorophenyl containing oxadiazoles. Eur. J. Med. Chem., 2008, 43(1), 25–31. DOI:https://doi.org/10.1016/j.ejmech.2007.03.013

10. Kaur H., Kumar S., Vishwakarma P., Sharma M. Synthesis and antipsychotic and anticonvulsant activity of some new substituted oxadiazolylazetidinonyl/thiazolidinonylcarbazoles. Eur. J. Med. Chem., 2010, 45(7), 2777–2783. DOI:https://doi.org/10.1016/j.ejmech.2010.02.060

11. Sharba A.H.K., Al-Bayati R.H., Aouad M. Synthesis of oxadiazoles, triazoles and triazole derived from benzo[b]thiophene. Molecules, 2005, 10(9), 1161–1168. DOI:https://doi.org/10.3390/10091161

12. Pitasse-Santos P., Sueth-Santiago V., Lima-Marco E.F. 1,2,4- and 1,3,4-Oxadiazoles as Scaffolds in the Development of Antiparasitic Agents. J. Braz. Chem. Soc., 2018, 29(3), 435–456. DOI:https://doi.org/10.21577/0103-5053.20170208

13. Li Z., Wang X. Synthesis and Biological Evaluation of 1,3,4-Oxadiazole Derivatives. Indian J. Chem., Sect. B, 2003, 42B, 941–944.

14. Rostom S.A.F., Shalaby M.A., El-Demellawy M.A. Design and Synthesis of Novel Anticancer Agents. Eur. J. Med. Chem., 2003, 38, 959–974. DOI:https://doi.org/10.1016/j.ejmech.2003.08.003

15. Nayak A.S., Baby G., Bhavani P.D., Madhukar G., Niharikha B., Sudha K. Design, microwave assisted synthesis and characterization of oxadiazoles. World J. Pharm. Res., 2023, 12, 991–995. DOI:https://doi.org/10.20959/wjpr202313-29065

16. Hedrick J.L., Twieg R. Design of High-Performance Polymers for Electronic Applications. Macromolecules, 1992, 25, 2021–2025. DOI:https://doi.org/10.1021/ma00033a028

17. Lam K.S., Salmon S.E., Hersh E.M., Hruby V.J., Kazmierski W.M., Knapp R.J. A New Type of Synthetic Peptide Library for Identifying Ligand-Binding Activity. Nature, 1991, 354, 82–84. DOI:https://doi.org/10.1038/354082a0

18. DeWitt S.H., Kiely J.S., Stankovic C.J., Schroeder M.C., Cody D.M.R., Pavia M.R. Diversomers – An Approach to Nonpeptide, Nonoligomeric Chemical Diversity. Proc. Natl. Acad. Sci. U.S.A., 1993, 90, 6909–6913. DOI:https://doi.org/10.1073/pnas.90.15.6909

19. Cankarova N., Krchnak V. Solid-Phase Synthesis Enabling Chemical Diversity. In: Diversity-Oriented Synthesis: Basics and Applications in Organic Synthesis, Drug Discovery, and Chemical Biology; Trabocchi A., Ed.; Wiley: N.Y., 2013, 201–252. DOI:https://doi.org/10.1002/9781118618110.ch7

20. Hwang J.Y., Choi H.S., Lee D.H., Gong Y.D. Solid-Phase Synthesis of 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Derivatives via Selective, Reagent-Based Cyclization of Acyldithiocarbazate Resins. J. Comb. Chem., 2005, 7, 816–819. DOI:https://doi.org/10.1021/cc0500957

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