Stabilizing Influence of Electron-Deficient Triazole Fragment on the Furan Heterocycle in Renewable Platform Chemicals
- Autores: Kolykhalov D.A.1, Golysheva A.N.1, Karlinskii B.Y.1,2
-
Afiliações:
- Tula State University
- N.D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences
- Edição: Volume 517, Nº 1 (2024)
- Páginas: 13-23
- Seção: CHEMISTRY
- URL: https://ter-arkhiv.ru/2686-9535/article/view/651899
- DOI: https://doi.org/10.31857/S2686953524040029
- EDN: https://elibrary.ru/YEDZME
- ID: 651899
Citar
Resumo
The effect of an aromatic triazole ring conjugated with a furan heterocycle on the stability of furan under various reaction conditions was studied, and a significant reduction in the degree of degradation of the electron-rich furan core and hydrolysis of the ester group under the action of a model acid and base in various organic solvents was shown. The lowest degree of degradation and hydrolysis of the triazole-substituted 2-furoic acid ester was achieved in dioxane, as well as in polar aprotic solvents (DMSO and DMF). It was shown that under the same conditions, a significant tarring and hydrolysis of the furan ester, which does not contain a conjugated triazole fragment, occurs.
Palavras-chave
Sobre autores
D. Kolykhalov
Tula State University
Email: karbo@ioc.ac.ru
Rússia, 300012 Tula
A. Golysheva
Tula State University
Email: karbo@ioc.ac.ru
Rússia, 300012 Tula
B. Karlinskii
Tula State University; N.D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences
Autor responsável pela correspondência
Email: karbo@ioc.ac.ru
Rússia, 300012 Tula; 119991 Moscow
Bibliografia
- Halkos G.E., Gkampoura E.-C. // Energies. 2020. V. 13. № 11. P. 2906. https://doi.org/10.3390/en13112906
- Seitkalieva M.M., Vavina A.V., Strukova E.N. // Dokl. Chem. 2023. V. 513. № 2. P. 380–388. https://doi.org/10.1134/s0012500823600967
- Redina E.A., Vikanova K.V., Tkachenko O.P., Kapustin G.I., Kustov L.M. // Dokl. Chem. 2022. V. 507. № 2. P. 261–269. https://doi.org/10.1134/s0012500822600158
- Zlotin S.G., Egorova K.S., Ananikov V.P., Akulov A.A., Varaksin M.V., Chupakhin O.N., Charushin V.N., Bryliakov K.P., Averin A.D., Beletskaya I.P., Dolengovski E.L., Budnikova Y.H., Sinyashin O.G., Gafurov Z.N., Kantyukov A.O., Yakhvarov D.G., Aksenov A.V., Elinson M.N., Nenajdenko V.G., Chibiryaev A.M., Nesterov N.S., Kozlova E.A., Martyanov O.N., Balova I.A., Sorokoumov V.N., Guk D.A., Beloglazkina E.K., Lemenovskii D.A., Chukicheva I.Y., Frolova L.L., Izmest’ev E.S., Dvornikova I.A., Popov A.V., Kutchin A.V., Borisova D.M., Kalinina A.A., Muzafarov A.M., Kuchurov I.V., Maximov A.L., Zolotukhina A.V. // Russ. Chem. Rev. 2023. V. 92. № 12. RCR5104. https://doi.org/10.59761/rcr5104
- Bozell J.J., Petersen G.R. // Green Chem. 2010. V. 12. № 4. P. 539–554. https://doi.org/10.1039/b922014c
- Bielski R., Grynkiewicz G. // Green Chem. 2021. V. 23. № 19. P. 7458–7487. https://doi.org/10.1039/d1gc02402g
- Espro C., Paone E., Mauriello F., Gotti R., Uliassi E., Bolognesi M.L., Rodríguez-Padrón D., Luque R. // Chem. Soc. Rev. 2021. V. 50. № 20. P. 11191–11207. https://doi.org/10.1039/d1cs00524c
- Gandini A., Lacerda T.M. // Macromol. Mater. Eng. 2022. V. 307. № 6. P. 2100902. https://doi.org/10.1002/mame.202100902
- Karlinskii B.Ya., Ananikov V.P. // Chem. Soc. Rev. 2023. V. 52. № 2. P. 836–862. https://doi.org/10.1039/d2cs00773h
- Jaswal A., Singh P.P., Mondal T. // Green Chem. 2022. V. 24. № 2. P. 510–551. https://doi.org/10.1039/d1gc03278j
- Najmidin K., Kerim A., Abdirishit P., Kalam H., Tawar T. // J. Mol. Model. 2013. V. 19. № 9. P. 3529–3535. https://doi.org/10.1007/s00894-013-1877-x
- Kucherov F.A., Romashov L.V., Galkin K.I., Ananikov V.P. // ACS Sustainable Chem. Eng. 2018. V. 6. № 7. P. 8064–8092. https://doi.org/10.1021/acssuschemeng.8b00971
- Rani M.A.A.B.A., Karim N.A., Kamarudin S.K. // Int. J. Energy Res. 2022. V. 46. № 13. P. 18996–19050. https://doi.org/10.1002/er.8545
- Averochkin G.M., Gordeev E.G., Skorobogatko M.K., Kucherov F.A., Ananikov V.P. // ChemSusChem 2021. V. 14. № 15. P. 3110–3123. https://doi.org/10.1002/cssc.202100818
- Shepelenko K.E., Nikolaeva K.A., Gnatiuk I.G., Garanzha O.G., Alexandrov A.A., Minyaev M.E., Chernyshev V.M. // Mendeleev Commun. 2022. V. 32. № 4. P. 485–487. https://doi.org/10.1016/j.mencom.2022.07.018
- Shepelenko K.E., Soliev S.B., Nikolaeva K.A., Minyaev M.E., Chernyshev V.M. // Russ. Chem. Bull. 2023. V. 72. № 8. P. 1746–1752. https://doi.org/10.1007/s11172-023-3956-1
- John I.G., Radom L. // J. Am. Chem. Soc. 1978. V. 100. № 13. P. 3981–3991. https://doi.org/10.1021/ja00481a001
- Cao H., Rupar P.A. // Chem. Eur. J. 2017. V. 23. № 59. P. 14670–14675. https://doi.org/10.1002/chem.201703355
- Karlinskii B.Ya., Romashov L.V., Galkin K.I., Kislitsyn P.G., Ananikov V.P. // Synthesis. 2019. V. 51. № 05. P. 1235–1242. https://doi.org/10.1055/s-0037-1610414
- Savelyeva N.Yu., Shpirt A.M., Orlova A.V., Chizhov A.O., Kononov L.O. // Russ. Chem. Bull. 2022. V. 71. № 8. P. 1784–1793. https://doi.org/10.1007/s11172-022-3590-3
- Johansson G., Sundquist S., Nordvall G., Nilsson B.M., Brisander M., Nilvebrant L., Hacksell U. // J. Med. Chem. 1997. V. 40. № 23. P. 3804–3819. https://doi.org/10.1021/jm970346t
- Hashmi A., Enns E., Frost T., Schäfer S., Frey W., Rominger F. // Synthesis. 2008. V. 2008. № 20. P. 3360–3360. https://doi.org/10.1055/s-0028-1083144
- Cui X., Xu X., Wojtas L., Kim M.M., Zhang X.P. // J. Am. Chem. Soc. 2012. V. 134. № 49. P. 19981–19984. https://doi.org/10.1021/ja309446n
- Fakhrutdinov A.N., Karlinskii B.Ya., Minyaev M.E., Ananikov V.P. // J. Org. Chem. 2021. V. 86. № 17. P. 11456–11463. https://doi.org/10.1021/acs.joc.1c00943
- Stini N.A., Gkizis P.L., Kokotos C.G. // Green Chem. 2022. V. 24. № 17. P. 6435–6449. https://doi.org/10.1039/d2gc02332f
- Warlin N., Garcia Gonzalez M.N., Mankar S., Valsange N.G., Sayed M., Pyo S.-H., Rehnberg N., Lundmark S., Hatti-Kaul R., Jannasch P., Zhang B. // Green Chem. 2019. V. 21. № 24. P. 6667–6684. https://doi.org/10.1039/c9gc03055g
- Hoang T.M.C., van Eck E.R.H., Bula W.P., Gardeniers J.G.E., Lefferts L., Seshan K. // Green Chem. 2015. V. 17. № 2. P. 959–972. https://doi.org/10.1039/c4gc01324g
- Tsilomelekis G., Orella M.J., Lin Z., Cheng Z., Zheng W., Nikolakis V., Vlachos D.G. // Green Chem. 2016. V. 18. № 7. P. 1983–1993. https://doi.org/10.1039/c5gc01938a
- Shen H., Shan H., Liu L. // ChemSusChem. 2020. V. 13. № 3. P. 513–519. https://doi.org/10.1002/cssc.201902799
- Hu X., Kadarwati S., Wang S., Song Y., Hasan M.D.M., Li C.-Z. // Fuel Process. Technol. 2015. V. 137. P. 212–219. https://doi.org/10.1016/j.fuproc.2015.04.024
- Motornov V., Pohl R., Klepetářová B., Beier P. // Chem. Commun. 2023. V. 59. № 61. P. 9364–9367. https://doi.org/10.1039/d3cc00987d
- Bauerová I., Ludwig M. // Collect. Czech. Chem. Commun. 2000. V. 65. № 11. P. 1777–1790. https://doi.org/10.1135/cccc20001777
- Nummert V., Piirsalu M., Mäemets V., Koppel I. // Collect. Czech. Chem. Commun. 2006. V. 71. № 1. P. 107–128. https://doi.org/10.1135/cccc20060107
- Mangione M.I., Spanevello R.A., Anzardi M.B. // RSC Adv. 2017. V. 7. № 75. P. 47681–47688. https://doi.org/10.1039/c7ra09558a
- Kozlov K.S., Romashov L.V., Ananikov V.P. // Green Chem. 2019. V. 21. № 12. P. 3464–3468. https://doi.org/10.1039/c9gc00840c
- Guan Y., Buivydas T., Lalisse R.F., Ali R., Hadad C.M., Mattson A.E. // Synthesis. 2022. V. 54. № 19. P. 4210–4219. https://doi.org/10.1055/a-1811-8075
Arquivos suplementares
