SYNTHESIS OF 6(PYRROLYL)-AZOLO[1,5-A]PYRIMIDINE-7-AMINES BY THE CLAUSION–KAAS METHOD

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Resumo

In this work, the synthesis of pyrrole derivatives based on azolo[1,5-a]pyrimidines (AP) using the Clauson–Kaas methodology is reported for the first time. It was found that within the series of azolo[1,5-a]- pyrimidine-6,7-diamines, the amino group at the 6-position reacts selectively. The developed method enables the synthesis of 6-(pyrrolyl)-[1,2,4]-azolo[1,5-a]pyrimidine-7-amines with yields of 64–85% and a high degree of purity. The reaction pathway is confirmed by NMR spectroscopy and X-ray structural analysis. The obtained results significantly expand the scope of azolopyrimidine modifications, opening new prospects for the targeted synthesis of functionalized derivatives.

Sobre autores

V. Fedotov

Ural Federal University named after the first President of Russia B.N. Yeltsin

Email: viktor.fedotov@urfu.ru
ul. Mira, 19, Ekaterinburg, 620062 Russia

S. Aminov

Ural Federal University named after the first President of Russia B.N. Yeltsin

ul. Mira, 19, Ekaterinburg, 620062 Russia

A. Neimash

Ural Federal University named after the first President of Russia B.N. Yeltsin

ul. Mira, 19, Ekaterinburg, 620062 Russia

D. Gazizov

Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

ul. Sofii Kovalevsko, 22/20, Ekaterinburg, 620066 Russia

A. Kultyshev

Ural Federal University named after the first President of Russia B.N. Yeltsin

ul. Mira, 19, Ekaterinburg, 620062 Russia

O. Eltsov

Ural Federal University named after the first President of Russia B.N. Yeltsin

ul. Mira, 19, Ekaterinburg, 620062 Russia

P. Slepukhin

Ural Federal University named after the first President of Russia B.N. Yeltsin; Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

ul. Mira, 19, Ekaterinburg, 620062 Russia; ul. Sofii Kovalevsko, 22/20, Ekaterinburg, 620066 Russia

E. Ulomsky

Ural Federal University named after the first President of Russia B.N. Yeltsin; Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

ul. Mira, 19, Ekaterinburg, 620062 Russia; ul. Sofii Kovalevsko, 22/20, Ekaterinburg, 620066 Russia

V. Rusinov

Ural Federal University named after the first President of Russia B.N. Yeltsin; Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

ul. Mira, 19, Ekaterinburg, 620062 Russia; ul. Sofii Kovalevsko, 22/20, Ekaterinburg, 620066 Russia

Bibliografia

  1. Sokolnikova T.V., Proidakov A.G., Penzik M.V., Kizhnyaev V.N., Russ. J. Org. Chem. 2024, 60, 1006–1012. doi: 10.1134/S1070428024060046
  2. Asati V., Anant A., Patel P., Kaur K., Gupta G.D., Eur. J. Med. Chem. 2021, 225, 113781. doi: 10.1016/j.ejmech.2021.113781
  3. Adawy H.A., Tawfik S.S., Elgazar A.A., Selim K.B., Goda F.E., RSC Adv. 2024, 14, 35239–35254. doi: 10.1039/D4RA06704E
  4. Pismataro M.C., Felicetti T., Bertagnin C., Nizi M.G., Bonomini A., Barreca M.L., Cecchetti V., Jochmans D., De Jonghe S., Neyts J., Loregian A., Tabarrini O., Massari S., Eur. J. Med. Chem. 2021, 221, 113494. doi: 10.1016/j.ejmech.2021.113494
  5. Chakrasali P., Hwang D., Lee J.-Y., Jung E., Lee H.L., Reneesh A., Skarka A., Musilek K., Nguyen N.H., Shin J.S., Jung, Y.-S., Eur. J. Med. Chem. 2024, 276, 116690. doi: 10.1016/j.ejmech.2024.116690
  6. Azeredo L.F.S.P., Coutinho J.P., Jabor V.A.P., Feliciano P.R., Nonato M.C., Kaiser C.R., Menezes C.M.S., Hammes A.S.O., Caffarena E.R., Hoelz L.V.B., De Souza N.B., Pereira G.A.N., Cerávolo I.P., Krettli A.U., Boechat N., Eur. J. Med. Chem. 2017, 126, 72–83. doi: 10.1016/j.ejmech.2016.09.073
  7. Zhuang J., Ma S., ChemMedChem 2020, 15, 1875–1886. doi: 10.1002/cmdc.202000378
  8. Ayman R., Abusaif M.S., Radwan A.M., Elmetwal- ly A.M., Ragab A., Eur. J. Med. Chem. 2023, 249, 115138. doi: 10.1016/j.ejmech.2023.115138
  9. Brigance R.P., Meng W., Fura A., Harrity T., Wang A., Zahler R., Kirby M.S., Hamann L.G., Bioorg. Med. Chem. Lett. 2010, 20, 4395–4398. doi: 10.1016/j.bmcl.2010.06.063
  10. Bouihi F., Schmaltz B., Mathevet F., Kreher D., Faure-Vincent J., Yildirim C., Elhakmaoui A., Bouclé J., Akssira M., Tran-Van F., Abarbri M., Materials 2022, 15, 7992. doi: 10.3390/ma15227992
  11. Tigreros A., Portilla J., RSC Adv. 2020, 10, 19693–19712. doi: 10.1039/D0RA02394A
  12. Tigreros A., Macías M., Portilla J., Dyes and Pigments 2021, 184, 108730. doi: 10.1016/j.dyepig.2020.108730
  13. Rote R.V., Shelar D.P., Patil S.R., Shinde S.S., To- che R.B., Jachak M.N., J. Fluoresc. 2011, 21, 453–459. doi: 10.1007/s10895-010-0704-3
  14. Salas J.M., Angustias Romero M., Purificación Sán- chez M., Quirós M., Coord. Chem. Rev. 1999, 193–195, 1119–1142. doi: 10.1016/S0010-8545(99)00004-1
  15. Castillo J.-C., Estupiñan D., Nogueras M., Cobo J., Portilla J., J. Org. Chem. 2016, 81, 12364–12373. doi: 10.1021/acs.joc.6b02431
  16. Aggarwal R., Kumar S., Virender Kumar A., Mohan B., Sharma D., Kumar V., Microchemical Journal 2022, 183, 107991. doi: 10.1016/j.microc.2022.107991
  17. Méndez-Arriaga J.M., Oyarzabal I., Escolano G., Rodríguez-Diéguez A., Sánchez-Moreno M., Salas J.M., J. Inorg. Biochem. 2018, 180, 26–32. doi: 10.1016/j.jinorgbio.2017.11.027
  18. Urakov G.V., Savateev K.V., Kotovskaya S.K., Rusi- nov V.L., Spasov A.A., Babkov D.A., Sokolova E.V., Molecules 2022, 27, 8697. doi: 10.3390/molecules27248697
  19. Pissot Soldermann C., Simic O., Renatus M., Erbel P., Melkko S., Wartmann M., Bigaud M., Weiss A., McSheehy P., Endres R., Santos P., Blank J., Schuffenhauer A., Bold G., Buschmann N., Zoller T., Alt- mann E., Manley P.W., Dix I., Buchdunger E., Scesa J., Quancard J., Schlapbach A., Bornancin F., Radimer- ski T., Régnier C.H., J. Med. Chem. 2020, 63, 14576–14593. doi: 10.1021/acs.jmedchem.0c01245
  20. Ushakova A.A., Fedotov V.V., Drokin R.A., Ulom- sky E.N., Rusinov V.L., Spasov A.A., Naumenko L.V., Taran A.S., Chebanko A.M., Yakovlev D.S., Pshenichnikova M.S., ChemistrySelect 2024, 9, e202404243. doi: 10.1002/slct.202404243
  21. Esteban-Parra G.M., Sebastián E.S., Cepeda J., Sánchez-González C., Rivas-García L., Llopis J., Aranda P., Sánchez-Moreno M., Quirós M., Rodríguez-Dié- guez A., J. Inorg. Biochem. 2020, 212, 111235. doi: 10.1016/j.jinorgbio.2020.111235
  22. Janke S., Boldt S., Nakielski P., Villinger A., Ehlers P., Langer P., J. Org. Chem. 2023, 88, 10470–10482. doi: 10.1021/acs.joc.3c00386
  23. Polkaehn J., Molenda R., Cordero M.A., Lochbrun- ner S., Boldt S., Ehlers P., Villinger A., Langer P., J. Org. Chem. 2024, 89, 2169–2181. doi: 10.1021/acs.joc.3c01772
  24. Singh P., Singh A., Singh D.K., Nath M., The Chemical Record 2024, 24, e202400112. doi: 10.1002/tcr.202400112
  25. Singh D.K., Kumar R., Beilstein J. Org. Chem. 2023, 19, 928–955. doi: 10.3762/bjoc.19.71.
  26. Bhardwaj V., Gumber D., Abbot V., Dhiman S., Shar- ma P., RSC Adv. 2015, 5, 15233–15266. doi: 10.1039/C4RA15710A
  27. Ahmad S., Alam O., Mohd. Naim J., Shaquiquz- zaman M., Alam M.M., Iqbal, M., Eur. J. Med. Chem. 2018, 157, 527–561. doi: 10.1016/j.ejmech.2018.08.002.
  28. Gazizov D.A., Fedotov V.V., Chistyakov K.A., Gorbunov E.B., Rusinov G.L., Charushin V.N., Tetrahedron 2021, 89, 132172. doi: 10.1016/j.tet.2021.132172

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