A New Approach to the Synthesis of [1,2,4]Triazolo[1,5-a]pyrimidines by Reaction of 1,2,4,5-Tetrazines with 2-Aminoxazoles

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

A new transformation of 3,6-diphenyl-1,2,4,5-tetrazine was discovered during the solvent-free reaction with 2-amino-4-aryloxazoles, leading to the formation of 2,5,7-triaryl[1,2,4]triazolo[1,5-a]pyrimidines. Stucture of products was also confirmed by single crystal X-ray diffraction data. A possible mechanism for this reaction was proposed.

Full Text

Restricted Access

About the authors

A. Rammohan

Ural Federal University

Email: a.p.krinochkin@urfu.ru
Russian Federation, Ekaterinburg, 620002

E. D. Ladin

Ural Federal University; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: a.p.krinochkin@urfu.ru
Russian Federation, Ekaterinburg, 620002; Ekaterinburg, 620219

Ya. K. Shtaitz

Ural Federal University

Email: a.p.krinochkin@urfu.ru
Russian Federation, Ekaterinburg, 620002

A. P. Krinochkin

Ural Federal University; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Author for correspondence.
Email: a.p.krinochkin@urfu.ru
Russian Federation, Ekaterinburg, 620002; Ekaterinburg, 620219

I. A. Khalymbadzha

Ural Federal University

Email: a.p.krinochkin@urfu.ru
Russian Federation, Ekaterinburg, 620002

P. A. Slepukhin

Ural Federal University; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: a.p.krinochkin@urfu.ru
Russian Federation, Ekaterinburg, 620002; Ekaterinburg, 620219

D. S. Kopchuk

Ural Federal University; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: a.p.krinochkin@urfu.ru
Russian Federation, Ekaterinburg, 620002; Ekaterinburg, 620219

G. V. Zyryanov

Ural Federal University; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: a.p.krinochkin@urfu.ru
Russian Federation, Ekaterinburg, 620002; Ekaterinburg, 620219

V. N. Charushin

Ural Federal University; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: a.p.krinochkin@urfu.ru
Russian Federation, Ekaterinburg, 620002; Ekaterinburg, 620219

V. Ch. Ranu

Ural Federal University

Email: a.p.krinochkin@urfu.ru
Russian Federation, Ekaterinburg, 620002

References

  1. Oukoloff K., Lucero B., Francisco K.R., Brunden K.R., Ballatore C. // Eur. J. Med. Chem. 2019. Vol. 165. P. 332. doi: 10.1016/j.ejmech.2019.01.027
  2. Łakomska I., Fandzloch M. // Coord. Chem. Rev. 2016. Vol. 327–328. P. 221. doi: 10.1016/j.ccr.2016.04.014
  3. Mohamed A.M., El-Sayed W.A., Ibrahim A.A., Abdel-Hafez N.A., Ali K.A.K., Mohamed S.F. // Org. Prep. Proced. Int. 2021. Vol. 53. N 3. P. 211. doi: 10.1080/00304948.2020.1871310
  4. Zhang N., Ayral-Kaloustian S., Nguyen T., Afragola J., Hernandez R., Lucas J., Gibbons J., Beyer C. // J. Med. Chem. 2007. Vol. 50. N 2. P. 319. doi: 10.1021/jm060717i
  5. Łakomska I., Hoffmann K., Wojtczak A., Sitkowski J., Maj E., Wietrzyk J. // J. Inorg. Biochem. 2014. Vol. 141. P. 188. doi: 10.1016/j.jinorgbio.2014.08.005
  6. Zuniga E.S., Korkegian A., Mullen S., Hembre E.J., Ornstein P.L., Cortez G., Biswas K., Kumar N., Cramer J., Masquelin T., Hipskind P.A., Odingo J., Parish T. // Bioorg. Med. Chem. 2017. Vol. 25. N 15. P. 3922. doi: 10.1016/j.bmc.2017.05.030
  7. Chen C.-N., Chen Q., Liu Y.-C., Zhu X.-L., Niu C.-W., Xi Z., Yang G.-F. // Bioorg. Med. Chem. 2010. Vol. 18. N 14. P. 4897. doi: 10.1016/j.bmc.2010.06.015
  8. Чупахин О.Н., Чарушин В.Н., Русинов В.Л., Уломский Е.Н., Котовская С.К., Киселев О.И., Деева Э.Г., Саватеев К.В., Борисов С.С. Пат. RU 2529487 C1 (2013); C. A. 2013. Vol. 161. P. 505376.
  9. Kolosov M.A., Shvets E.H., Manuenkov D.A., Vlasenko S.A., Omel’chenko I.N., Shishkina S.V., Orlov V.D. // Tetrahedron Lett. 2017. Vol. 58. N 12. P. 1207. doi: 10.1016/j.tetlet.2017.02.035.
  10. Stanovnik B., Urleb U., Tigler M. // Monatsh. Chem. 1987. Vol. 118. P. 601. doi: 10.1007/BF00809671
  11. Газизов Д.А., Федотов В.В., Горбунов Е.Б., Уломский Е.Н., Ельцов О.С., Русинов Г.Л., Русинов В.Л. // ХГС. 2019. Т. 55. № 6. С. 573; Gazizov D.A., Fedotov V.V., Gorbunov E.B., Ulomskiy E.N., Yeltsov O.S., Rusinov G.L., Rusinov V.L. // Chem. Heterocycl. Compd. 2019. Vol. 55. N 6. P. 573. doi: 10.1007/s10593-019-02498-2
  12. Omar F.A., El-Koussi N.A., Radwan M.F., Abdel-Aziz S.A. // Bull. Pharm. Sci. Assiut University. 2004. Vol. 27. P. 141.
  13. Bartels B., Bolas C.G., Cueni P., Fantasia S., Gaeng N., Trita A.S. // J. Org. Chem. 2015. Vol. 80. N 2. P. 1249. doi: 10.1021/jo502536t
  14. Gilandoust M., Harsha K.B., Mohan C.D., Raqui A.R., Rangappa S., Pandey V., Lobie P.E., Basappa, Rangappa K.S. // Bioorg. Med. Chem. Lett. 2018. Vol. 28. N 13. P. 2314. doi: 10.1016/j.bmcl.2018.05.020
  15. El Khadem H., Kawai J., Swartz D.L. // Heterocycles. 1989. Vol. 28. P. 239. doi: 10.3987/COM-88-S4
  16. Song L., Tian X., Lv Z., Li E., Wu J., Liu Y., Yu W., Chang J. // J. Org. Chem. 2015. Vol. 80. P. 7219. doi: 10.1021/acs.joc.5b01183
  17. Прохоров А.М., Кожевников Д.Н. // ХГС. 2012. № 8. С. 1237; Prokhorov A.M., Kozhevnikov D.N. // Chem. Heterocycl. Compd. 2012. Vol. 48. N 8. P. 1153. doi: 10.1007/s10593-012-1117-9
  18. Miomandre F., Audebert P. // J. Photochem. Photobiol. (C). 2020. Vol. 44. Article no. 100372.
  19. Rickborn B. // Org. React. 1998. Vol. 53. P. 223. doi: 10.1002/0471264180.or052.01
  20. Zhu Z., Glinkerman C.M., Boger D.L. // J. Am. Chem. Soc. 2020. Vol. 142. N 49. P. 20778. doi: 10.1021/jacs.0c09775
  21. Soenen D.R., Zimpleman J.M., Boger D.L. // J. Org. Chem. 2003. Vol. 68. N 9. P. 3593. doi: 10.1021/jo020713v
  22. Suh S.-E., Chenoweth D.M. // Org. Lett. 2016. Vol. 18. N 16. P. 4080. doi: 10.1021/acs.orglett.6b01977
  23. Boger D.L., Schaum R.P., Garbaccio R.M. // J. Org. Chem. 1998. Vol. 63. N 18. P. 6329. doi: 10.1021/jo980795g
  24. Oakdale J.S., Boger D.L. // Org. Lett. 2010. Vol. 12. N 5. P. 1132. doi: 10.1021/ol100146b
  25. Krinochkin A.P., Reddy G.M., Kopchuk D.S., Slepukhin P.A., Shtaitz Y.K., Khalymbadzha I.A., Kovalev I.S., Kim G.A., Ganebnykh I.N., Zyryanov G.V., Chupakhin O.N., Charushin V.N. // Mendeleev Commun. 2021. Vol. 31. N 4. P. 542. doi: 10.1016/j.mencom.2021.07.035
  26. Раммохан А., Криночкин А.П., Копчук Д.С., Штайц Я.К., Ковалев И.С., Савчук М.И., Зырянов Г.В., Русинов В.Л., Чупахин О.Н. // ЖОрХ. 2022. Т. 58. № 2. С. 127; Rammohan A., Krinochkin A.P., Kopchuk D.S., Shtaitz Ya.K., Kovalev I.S., Savchuk M.I., Zyryanov G.V., Rusinov V.L., Chupakhin O.N. // Russ. J. Org. Chem. 2022. Vol. 58. N 2. P. 175. doi: 10.1134/S1070428022020026
  27. Раммохан А., Штайц Я.К., Ладин Е.Д., Криночкин А.П., Слепухин П.А., Шарутин В.В., Шарафиева Э.Р., Поспелова Т.А., Копчук Д.С., Зырянов Г.В. // ЖОХ. 2023. Т. 93. № 2. С. 200; Rammohan A., Shtaitz Ya.K., Ladin E.D., Krinochkin A.P., Slepukhin P.A., Sharutin V.V., Sharafieva E.R., Pospelova T.A., Kopchuk D.S., Zyryanov G.V. // Russ. J. Gen. Chem. 2023. Vol. 93. N 2. P. 263. doi: 10.1134/S1070363223020056
  28. Раммохан А., Криночкин А.П., Копчук Д.С., Штайц Я.К., Шарафиева Э.Р., Гавико В.С., Зырянов Г.В., Чупахин О.Н. // ЖОрХ. 2023. Т. 59. № 9. С. 1233; Rammohan A., Krinochkin A.P., Kopchuk D.S., Shtaitz Ya.K., Sharafieva E.R., Gaviko V.S., Zyryanov G.V., Chupakhin O.N. // Russ. J. Org. Chem. 2023. Vol. 59. N 9. P. 1633. doi: 10.1134/S1070428023090233
  29. Seitz G., Mohr R., Hoferichter R. // Cheminform. 1989. Vol. 20. N 28. Article no. 235. doi: 10.1002/chin.198928235
  30. Sieburth S. Mc N. // e-EROS Encyclopedia of Reagents for Organic Synthesis. doi: 10.1002/047084289X.ro018
  31. Seitz G., Hoferichter R., Mohr R. // Chem. Zeit. 1989. Vol. 322. N 7. P. 415. doi: 10.1002/ardp.19893220707
  32. El-Koussi N.A., Omar F.A., Abdel-Aziz S.A., Radwan M.F. // Bull. Pharm. Sci. 2004. Vol. 27. P. 141-154.
  33. Rasputin N.A., Demina N.S., Irgashev R.A., Shchepochkin A.V., Rusinov G.L., Chupakhin O.N., Charushin V.N. // Arkivoc. 2020. N 6. P. 330. doi: 10.24820/ark.5550190.p011.247
  34. Hu W.-X., Rao G.-W., Sun Y.-Q. // Bioorg. Med. Chem. Lett. 2004. Vol. 14. P. 1177. doi: 10.1016/j.bmcl.2003.12.056
  35. Wu J.H., Tian X., Liu W. Pat. WO 2016049774 A1 (2016); C. A. 2016. Vol. 164. P. 472391.
  36. Borman R.A., Coleman R.A., Clark K.L., Oxford A.W., Hynd G., Archer J.A., Aley A., Harris N.V. Pat. WO 2005012263 A1 (2005); C. A. 2005. Vol. 142. P. 219297.
  37. CrysAlisPro, version 1.171.39.38a, Data Collection, Reduction and Correction Program, Rigaku Oxford Diffraction, 2017.
  38. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H. // J. Appl. Cryst. 2009. Vol. 42. N 2. P. 339. doi: 10.1107/S0021889808042726.
  39. Sheldrick G.M. // Acta Crystallogr. (C). 2015. Vol. 71. N 1. P. 3. doi: 10.1107/S2053229614024218.
  40. Деева Э.Г., Шевчик Ю.И., Шалджан А.А., Загородникова К.А., Тумашов А.А., Баклыков А.В., Котовская С.К., Чупахин О.Н., Чарушин В.Н., Русинов В.Л., Копчук Д.С. // Разработка и регистрация лекарственных средств. 2018. Т. 3. № 24. С. 172.

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Fig. 1. The structure of compound 3a according to the RSA data in the representation of thermal ellipsoids with a 50% probability.

Download (92KB)
Indexing metadata
3. Fig. 2. Shortened π–π contacts in the junction 3a crystal (distances are indicated in Å).

Download (109KB)
Indexing metadata
4. Scheme 1.

Download (62KB)
Indexing metadata
5. Scheme 2.

Download (266KB)
Indexing metadata

Copyright (c) 2024 Russian Academy of Sciences

This website uses cookies

You consent to our cookies if you continue to use our website.

About Cookies