Синтез 3-алкенил(пропаргил)сульфанил-5,6дифенил-1,2,4-триазинов и их исследование методами ЯМР и масс-спектрометрии
DOI:
https://doi.org/10.17072/2223-1838-2019-4-396-406Ключевые слова:
5,6-дифенил-2,3-дигидро-1,2,4-триазин-3-тион, 5,6-дифенил-3-алкенилсульфанил- 1,2,4-триазин, 5,6-дифенил-3-пропаргил-1,2,4-триазин, алкилирование, масс-спектрометрия, ЯМРАннотация
Взаимодействием 5,6-дифенил-2,3-дигидро-1,2,4-триазин-3-тиона с алкилгалогенидами синтезирован ряд 3-алкенил(пропаргил)сульфанил-5,6-дифенил-1,2,4-триазинов., строение которых исследовано методами ЯМР 1Н, 13С и масс-спектрометрииБиблиографические ссылки
Библиографический список
Abdel-Rahman R. M., Ghareib M. Synthesis and Biological Activities of Some New 3-Substituted 5,6-Diphenyl-1,2,4-triazines // Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry. 1987. Vol. 26. P. 496–500.
Tang X., Su S., Chen M., He J., Xia R., Guo T., Chen Y., Zhang C., Wang J., Xue W. Novel chalcone derivatives containing a 1,2,4-triazine moiety: design, synthesis, antibacterial and an-tiviral activities //, RSC Adv. 2019. Vol. 6. P. 6011.
Fu D.-J., Song J., Hou Y.-H., Zhao R.-H., Li J.-H., Mao W., Yang J.-J., Li P., Zi X.-L., Li Z.-H., Zhang Q.-Q., Wang F.-Y., Zhang S.-Y., Zhang Y.-B., Liu H.-M. Discovery of 5,6-diaryl-1,2,4-triazines hybrids as potential apoptosis inducers // European Journal of Medicinal Chemistry. 2017. Vol. 138. P. 1076–1088.
Wang G., Li X., Wang J., Xie Z., Li L., Chen M., Chen S., Peng Y. Synthesis, molecular docking and a-glucosidase inhibition of 2 ((5,6-diphenyl-1,2,4-triazin-3-yl)thio)-N-arylacetamides / // Bioorganic & Medicinal Chemistry Letters. 2017. Vol. 27. P. 1115–1118.
Irannejad Н., Amini M., Khodagholi F., Ansari N., Khoramian Tusi S., Sharifzadeh M., Shafiee A. Synthesis and in vitro evaluation of novel 1,2,4-triazine derivatives as neuroprotective agents // Bioorganic and Medicinal Chemistry. 2010. Vol. 18. P. 4224–4230.
Gupta A.K., Rastogi A., Hajela K.S. Synthesis and Acetylcholinesterase Activity of 1-aryl-3-(3,4-diphenyl-1,2,4-triazine-6-ylmercaptoacetyl)ureas // Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry. 1983. Vol. 22, № 10. P. 1074–1075.
Irannejad H., Naderi N., Emami S., Ghadikolaei R.Q., Foroumadi A., Zafari T., Mazar-Atabaki A., Dadashpour S. Microwave-assisted synthesis and anticonvulsant activity of 5,6 bisaryl-1,2,4-triazine-3-thiol derivatives // Medical Chemistry Research. 2013. Vol. 23. P. 2503–2514.
Nassar Ibrahim F. Synthesis and Antitumor Activity of New Substituted Mercapto-1,2,4-Triazine Derivatives, Their Thioglycosides, and Acyclic Thioglycoside Analogs // J. Heterocy-clic Chem. 2013. Vol. 50, Р. 129.
Yazdania M., Yazdani M., Edrakic N., Badrib R., Khoshneviszadehc M., Irajic A., Firuzic O. Multi-target inhibitors against Alzheimer disease derived from 3-hydrazinyl 1,2,4-triazine scaf-fold containing pendant phenoxy methyl-1,2,3-triazole: Design, synthesis and biological evalu-ation // Bioorganic Chemistry. 2019. Vol. 84. P. 363–371.
Tamboli R.S., Giridhar R., Mande H.M., Shah S.R., Yadav M.R. Room-Temperature Ionic Liq-uid–DMSO Promoted and Improved One-Pot Synthesis of 5,6-Diaryl-1,2,4-triazines // Synthet-ic Communications. 2014. Vol. 44. P. 2192–2204.
Kopchuk D.S., Chepchugov N.V., Kim G.A., Zyryanov G.V., Kovalev I.S., Rusinov V.L., Chupakhina O.N. Synthesis of unsymmetric 6,6´diaryl2,2´bipyridines using a 1,2,4-triazine methodology // Russian Chemical Bulletin. 2015. Vol. 64, № 3. P. 695–698.
Fu D.-J., Li P., Wu B.-W., Cui X.-X., Zhao C.-B., Zhang S.-Y. Molecular diversity of trimethox-yphenyl-1,2,3-triazole hybrids as novel colchicine site tubulin polymerization inhibitors // Eu-ropean Journal of Medicinal Chemistry. 2019. Vol. 165. P. 309–322.
Wang G., Peng Z., Wang J., Li X., Li J. Synthesis, in vitro evaluation and molecular docking studies of novel triazine-triazole derivatives as potential α-glucosidase inhibitors // European Journal of Medicinal Chemistry. 2017. Vol. 125. P. 423–429.
Теренин В.И. Практикум по органической химии: учеб. пособие // М.: Лаборатория знаний, 2015. 571 с.
Habibi D., Vakili S. Nano Sized silica supported FeCl3 as an efficient heterogeneous catalyst for the synthesis of 1,2,4-triazine derivatives // Chinese Journal of Catalysis. 2015. Vol. 36. P. 620–625.
