Skip to main content
Log in

Synthesis and Phosphonylation of 6-Amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A series of 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles was synthesized, further reaction of which with dimethyl chloroethynylphosphonate yielded a series of new dimethyl (8-cyano-7-aryl-5-thioxo-5,6-dihydroimidazo[1,2-c]pyrimidin-2-yl)phosphonates.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme
Scheme
Scheme
Scheme

REFERENCES

  1. Kobak, R.Z. and Akkurt, B., J. Turkish Chem. Soc. (A), 2022, vol. 9, no. 4, p. 1335. https://doi.org/10.18596/jotcsa.1110922/

    Article  CAS  Google Scholar 

  2. Zarenezhad, E., Farjam, M., and Iraji, A., J. Mol. Struct., 2021, vol. 1230, p. 129833. https://doi.org/10.1016/j.molstruc.2020.129833

    Article  CAS  Google Scholar 

  3. Pankin, D., Khokhlova, A., Kolesnikov, I., Vasileva, A., Pilip, A., Egorova, A., Erkhitueva, E., Zigel, V., Gureev, M., and Manshina, A., Spectrochim. Acta (A), 2021, vol. 246, p. 118979. https://doi.org/10.1016/j.saa.2020.118979

    Article  CAS  Google Scholar 

  4. Rogova, A., Gorbunova, I.A., Karpov, T.E., Sidorov, R.Yu., Rubtsov, A.E., Shipilovskikh, D.A., Muslimov, A.R., Zyuzin, M.V., Timin, A.S., and Shipilovskikh, S.A., Eur. J. Med. Chem., 2023, vol. 254, p. 115325. https://doi.org/10.1016/j.jcis.2021.09.031

    Article  CAS  PubMed  Google Scholar 

  5. Yang, J., Liu, D., Lu, T., Sun, H., Li, W., Testoff, T.T., Zhou, X., and Wang, L., Quantum Chem., 2020, vol. 120, no. 19, p. e26355. https://doi.org/10.1002/qua.26355

  6. Tigreros, A., Aranzazu, S.-L., Ríos, M.-C., and Portilla, J., Eur. J. Org. Chem., 2023, vol. 26, no. 15, p. e202300089. https://doi.org/10.1002/ejoc.202300089

  7. Verbitskiy, E.V., Steparuk, A.S., Zhilina, E.F., Emets, V.V., Grinberg, V.A., Krivogina, E.V., Kozyukhin, S.A., Belova, E.V., Lazarenko, P.I., Rusinov, G.L., Tameev, A.R., Nunzi, J.M., and Charushin, V.N., Electron. Mater., 2021, vol. 2, no. 2, p. 142. https://doi.org/10.3390/electronicmat2020012

    Article  Google Scholar 

  8. Verbitskiy, E.V., Cheprakova, E.M., Subbotina, J.O., Schepochkin, A.V., Slepukhin, P.A., Rusinov, G.L., Charushin, V.N., Chupakhin, O.N., Makarova, N.I., Metelitsa, A.V., and Minkin, V.I., Dyes Pigm., 2014, vol. 100, p. 201. https://doi.org/10.1016/j.dyepig.2013.09.006

    Article  CAS  Google Scholar 

  9. Yadav, A.K., Ghule, V.D., and Dharavath, S., J. Mater. Chem. (A), 2022, vol. 10, no. 23, p. 12702. https://doi.org/10.1039/D2TA02042D

    Article  CAS  Google Scholar 

  10. Torkildsen, L., Samuelsen, O.B., Lunestad, B.T., and Bergh, Ø., Aquaculture, 2000, vol. 185, nos. 1–2, p. 1. https://doi.org/10.1016/S0044-8486(99)00338-5

    Article  CAS  Google Scholar 

  11. Tollemeto, G. and Cardamone, S., Minerva Ginecologica, 1983, vol. 35, nos. 1–2, p. 47.

    CAS  PubMed  Google Scholar 

  12. Drover, D.R., Clin. Pharmacokinetics, 2004, vol. 43, p. 227. https://doi.org/10.2165/00003088-200443040-00002

    Article  CAS  Google Scholar 

  13. Petroski, R.E., Pomeroy, J.E., Das, R., Bowman, H., Yang, W., Chen, A.P., and Foster, A.C., J. Pharm. Exp. Therap., 2006, vol. 317, no. 1, p. 369. https://doi.org/10.1124/jpet.105.096701

    Article  CAS  Google Scholar 

  14. Vinkers, C.H., Olivier, B., Hanania, T., Min, W., Schreiber, R., Hopkins, S.C., Campbell, U., and Paterson, N., Eur. J. Pharmacol., 2011, vol. 668, nos. 1–2, p. 190. https://doi.org/10.1016/j.ejphar.2011.06.054

    Article  CAS  PubMed  Google Scholar 

  15. Agarwal, V., Hans, N., and Messerli, F.H., J. Clin. Hypertension, 2012, vol. 15, no. 6, p. 435. https://doi.org/10.1111/j.1751-7176.2012.00701.x

    Article  CAS  Google Scholar 

  16. Langtry, H.D. and Benfield, P., Drugs, 1990, vol. 40, p. 291. https://doi.org/10.2165/00003495-199040020-00008

    Article  CAS  PubMed  Google Scholar 

  17. Mizushige, K., Ueda, T., Yukiiri, K., and Suzuki, H., Cardiovascular Drug Rev., 2006, vol. 20, no. 3, p. 163. https://doi.org/10.1111/j.1527-3466.2002.tb00085.x

    Article  Google Scholar 

  18. Simon, W.A., Herrmann, M., Klein, T., Shin, J.M., Huber, R., Senn-Bilfinger, J., and Postius, S., J. Pharm. Exp. Ther., 2007, vol. 321, no. 3, p. 866. https://doi.org/10.1124/jpet.107.120428

    Article  CAS  Google Scholar 

  19. Sanger, D.J., Joly, D., and Perrault, G., Psychopharmacol., 1995, vol. 121, p. 104. https://doi.org/10.1007/BF02245596

    Article  CAS  Google Scholar 

  20. Egorov, D.M., Piterskaya, Yu.L., Erkhitueva, E.B., Svintsitskaya, N.I., and Dogadina, A.V., Russ. J. Gen. Chem., 2017, vol. 87, no. 9, p. 1924. https://doi.org/10.1134/S1070363217090067

    Article  CAS  Google Scholar 

  21. Erkhitueva, E.B., Panikorovskii, T.L., Svintsitskaya, N.I., Trifonov, R.Е., and Dogadina, А.V., Synlett, 2018, vol. 29, no. 7, p. 933. https://doi.org/10.1055/s-0036-1591919

    Article  CAS  Google Scholar 

  22. Krylov, A.S., Petrosian, A.A., Piterskaya, J.L., Svintsitskaya, N.I., and Dogadina, A.V., Beilstein J. Org. Chem., 2019, vol. 15, p. 1563. https://doi.org/10.3762/bjoc.15.159

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Kaskevich, K.I., Babushkina, A.A., Gurzhiy, V.V., Egorov, D.M., Svintsitskaya, N.I., and Dogadina, A.V., Beilstein J. Org. Chem., 2020, vol. 16, p. 1947. https://doi.org/10.3762/bjoc.16.161

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. Babushkina, A.A., Dogadina, A.V., Egorov, D.M., Piterskaia, J.L., Shtro, A.A., Nikolaeva, Y.V., Galochkina, A.V., Kornev, A.A., and Boitsov, V.M., Med. Chem. Res., 2021, vol. 30, no. 12, p. 2203. https://doi.org/10.1007/s00044-021-02801-x

    Article  CAS  Google Scholar 

  25. Egorova, A.V., Viktorov, N.B., Starova, G.L., Svintsitskaya, N.I., Garabadziu, A.V., and Dogadina, A.V., Tetrahedron Lett., 2017, vol. 58, no. 30, p. 2997. https://doi.org/10.1016/j.tetlet.2017.06.062

    Article  CAS  Google Scholar 

  26. Mashhada, H.A., Soukhtanloob, M., and Massoudi, A., Bioorg. Chem., 2016, vol. 42, p. 316. https://doi.org/10.1134/S1068162016020047

    Article  CAS  Google Scholar 

  27. Ayman, M.S., Fouda, A.M., and Rasha, M.F., Chem. Central J., 2018, vol. 12, p. 202. https://doi.org/10.1186/s13065-018-0419-0

    Article  CAS  Google Scholar 

  28. Fadda, A.A., El-Latif, E.A., Bondock, S., and Samir, A., Synth. Commun., 2008, vol. 38, no. 24, p. 4352. https://doi.org/10.1080/00397910802326596

    Article  CAS  Google Scholar 

  29. Ghodasara, H.B., Trivedi, A.R., Kataria, V.B., Patel, B.G., and Shah, V.H., Med. Chem. Res., 2013, vol. 22, p. 6121. https://doi.org/10.1007/s00044-013-0596-2

    Article  CAS  Google Scholar 

  30. Filimonov, D.A., Druzhilovskiy, D.S., Lagunin, A.A., Gloriozova, T.A., Rudik, A.V., Dmitriev, A.V., Pogodin, P.V., and Poroikov, V.V., Biomed. Chem. Res. Meth., 2018, vol. 1, no. 1, p. e00004. https://doi.org/10.18097/BMCRM00004

  31. Stolbov, L., Druzhilovskiy, D., Rudik, A., Filimonov, D., Poroikov, V., and Nicklaus, M., Bioinformatics, vol. 36, no. 3, p. 978. https://doi.org/10.1093/bioinformatics/btz638

  32. Filimonov, D.A., Lagunin, A.A., Gloriozova, T.A., Rudik, A.V., Druzhilovskii, D.S., Pogodin, P.V., and Poroikov, V.V., Chem. Heterocycl. Compd., 2014, vol. 50, no. 3, p. 444. https://doi.org/10.1007/s10593-014-1496-1

    Article  CAS  Google Scholar 

  33. Egorov, D.M., Babushkina, A.A., Leonenok, V.E., Chekalov, A.P., and Piterskaya, Yu.L., Russ. J. Gen. Chem., 2020, vol. 90, no. 2, p. 319. https://doi.org/10.1134/S1070363220020267

    Article  CAS  Google Scholar 

  34. Nosova, N.A., Skrylkova, A.S., and Egorov, D.M., Russ. J. Gen. Chem., 2023, vol. 93, no. 9, p. 2230. https://doi.org/10.1134/S1070363223090062

    Article  CAS  Google Scholar 

  35. Krylov, A.S., Kaskevich, K.I., Erkhitueva, E.B., Svintsitskaya, N.I., and Dogadina, A.V., Tetrahedron Lett., 2018, vol. 59, no. 49, p. 4326. https://doi.org/10.1016/j.tetlet.2018.10.052

    Article  CAS  Google Scholar 

Download references

Funding

This work was financially supported by the Russian Science Foundation (grant no. 23-13-00224, https://rscf.ru/project/23-13-00224/) using the equipment of the Engineering Center of the St. Petersburg State Institute of Technology.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to D. M. Egorov.

Ethics declarations

The authors declare no conflict of interest.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nosova, N.A., Fatuev, E.D., Krylov, A.S. et al. Synthesis and Phosphonylation of 6-Amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles. Russ J Gen Chem 93, 3081–3088 (2023). https://doi.org/10.1134/S1070363223120071

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363223120071

Keywords:

Navigation