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Efficient Synthesis of Pyrido[2,3-d]pyrimidines by Recyclization of N-Arylitaconimides with Aminopyrimidinones

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Abstract

A convenient method has been proposed for the synthesis of 2-(4,7-dioxopyrido[2,3-d]pyrimidin-6-yl)acetanilides and 2-(2,4,7-trioxopyrido[2,3-d]pyrimidin-6-yl)acetanilides via reaction of N-arylitaconimides with 6-aminopyrimidin-4(3H)-ones and 6-aminopyrimidine-2,4(1H,3H)-diones, respectively, in boiling acetic acid.

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REFERENCES

  1. Moreno, E., Plano, D., Lamberto, I., Font, M., Encío, I., Palop, J.A., and Sanmartín, C., Eur. J. Med. Chem., 2012, vol. 47, p. 283. https://doi.org/10.1016/j.ejmech.2011.10.056

    Article  CAS  PubMed  Google Scholar 

  2. Flefel, E.M., Sayed, H.H., Hashem, A.I., Shalaby, E.A., El-Sofany, W., and Abdel-Megeid, F.M.E., Med. Chem. Res., 2014, vol. 23, p. 2515. https://doi.org/10.1007/s00044-013-0830-y

    Article  CAS  Google Scholar 

  3. Krapf, M.K., Gallus, J., Vahdati, S., and Wiese, M., J. Med. Chem., 2018, vol. 61, p. 3389. https://doi.org/10.1021/acs.jmedchem.7b01012

    Article  CAS  PubMed  Google Scholar 

  4. Gangjee, A., Vasudevan, A., Queener, S.F., and Kisliuk, R.L., J. Med. Chem., 1995, vol. 38, p. 1778. https://doi.org/10.1021/jm00010a022

    Article  CAS  PubMed  Google Scholar 

  5. Lakshmi Narayana, B., Raghu Ram Rao, A., and Shanthan Rao, P., Eur. J. Med. Chem., 2009, vol. 44, p. 1369. https://doi.org/10.1016/j.ejmech.2008.05.025

    Article  CAS  PubMed  Google Scholar 

  6. Elagamey, A.G., Abdel Sattar, S., El-Taweel, F., and Said, S., J. Heterocycl. Chem., 2016, vol. 63, p. 1801. https://doi.org/10.1002/jhet.2487

    Article  CAS  Google Scholar 

  7. El-Gazzar Abdel-Rahman, B.A., El-Enanyb, M.M., and Mahmoud, N.M., Bioorg. Med. Chem., 2008, vol. 16, p. 3261. https://doi.org/10.1016/j.bmc.2007.12.012

    Article  CAS  PubMed  Google Scholar 

  8. Hanafy, F.I., Eur. J. Chem., 2011, vol. 2, p. 65. https://doi.org/10.5155/eurjchem.2.1.65-69.303

    Article  CAS  Google Scholar 

  9. Buron, F., Merour, J.Y., Akssira, M., Guillaumet, G., and Routier, S., Eur. J. Med. Chem., 2015, vol. 95, p. 76. https://doi.org/10.1016/j.ejmech.2015.03.029

    Article  CAS  PubMed  Google Scholar 

  10. Mont, N., Teixidó, J., Borrella, J.I., and Kappe, C.O., Tetrahedron Lett., 2003, vol. 44, p. 5385. https://doi.org/10.1016/S0040-4039(03)01306-6

    Article  CAS  Google Scholar 

  11. Kumar, N., Singh, G., and Yadav, A.K., Heteroat. Chem., 2001, vol. 12, p. 52. https://doi.org/10.1002/1098-1071(2001)12:1<52::AID-HC11>3.0.CO;2-0

    Article  CAS  Google Scholar 

  12. Gangjee, A., Adaira, O., and Queener, S.F., Bioorg. Med. Chem., 2001, vol. 9, p. 2929. https://doi.org/10.1016/S0968-0896(01)00223-1

    Article  CAS  PubMed  Google Scholar 

  13. Ibrahim, D.A. and Ismail, N.S.M., Eur. J. Med. Chem., 2011, vol. 46, p. 5825. https://doi.org/10.1016/j.ejmech.2011.09.041

    Article  CAS  PubMed  Google Scholar 

  14. Chebanov, V.A., Saraev, V.E., Gura, E.A., Desenko, S.M., and Musatov, V.I., Collect. Czech. Chem. Commun., 2005, vol. 70, p. 350. https://doi.org/10.1135/cccc20050350

    Article  CAS  Google Scholar 

  15. Hassan, N.A., Hegab, M.I., Hashem, A.I., AbdelMotti, F.M., Hebah, S.H.A., and Abdel-Megeid, F.M.E., J. Heterocycl. Chem., 2007, vol. 44, p. 775. https://doi.org/10.1002/jhet.5570440404

    Article  CAS  Google Scholar 

  16. Takahashi, M., Nagaoka, H., and Inoue, K., J. Heterocycl. Chem., 2004, vol. 41, p. 525. https://doi.org/10.1002/jhet.5570410408

    Article  CAS  Google Scholar 

  17. Devi, I., Borah, H.N., and Bhuyan, P.J., Tetrahedron Lett., 2004, vol. 45, p. 2405. https://doi.org/10.1016/j.tetlet.2004.01.094

    Article  CAS  Google Scholar 

  18. Rudenko, R.V., Komykhov, S.A., Desenko, S.M., Sen’ko, Y.V., Shishkin, O.V., Konovalova, I.S., Shishkina, S.V., and Chebanov, V.A., Synthesis, 2011, vol. 2011, no. 19, p. 3161. https://doi.org/10.1055/s-0030-1260163

    Article  CAS  Google Scholar 

  19. Rudenko, R.V., Komykhov, S.A., and Desenko, S.M., Chem. Heterocycl. Compd., 2009, vol. 45, p. 1017. https://doi.org/10.1007/s10593-009-0377-5

    Article  CAS  Google Scholar 

  20. Metwally, M.A., Farahat, A.A., and Abdel-Wahab, B.F., J. Sulfur Chem., 2010, vol. 31, p. 315. https://doi.org/10.1080/17415993.2010.482155

    Article  CAS  Google Scholar 

  21. Shikhaliev, Kh.S., Kovygin, Yu.A., Potapov, A.Yu., Sabynin, A.L., and Kosheleva, E.A., Russ. Chem. Bull., Int. Ed., 2017, vol. 66, p. 86. https://doi.org/10.1007/s11172-017-1704-0

    Article  CAS  Google Scholar 

  22. Rudenko, R.V., Komykhov, S.A., Desenko, S.M., Musatov, V.I., Shishkin, O.V., Konovalova, I.S., Vashchenko, E.V., and Chebanov, V.A., Synthesis, 2011, vol. 2011, no. 5, p. 783. https://doi.org/10.1055/s-0030-1258421

    Article  CAS  Google Scholar 

  23. Vandyshev, D.Yu., Shikhaliev, Kh.S., Potapov, A.Yu., and Krysin, M.Yu., Chem. Heterocycl. Compd., 2015, vol. 51, p. 829. https://doi.org/10.1007/s10593-015-1782-6

    Article  CAS  Google Scholar 

  24. Lin, S., Leow, D., Huang, K., and Tan, C., Chem. Asian J., 2009, vol. 4, p. 1741. https://doi.org/10.1002/asia.200900331

    Article  CAS  PubMed  Google Scholar 

  25. Zhu, B., Lee, R., Li, J., Ye, X., Hong, S., Qiu, S., Coote, M.L., and Jiang, Z., Angew. Chem., Int. Ed., 2016, vol. 55, p. 1299. https://doi.org/10.1002/anie.201507796

    Article  CAS  Google Scholar 

  26. Kovygin, Yu.A., Shikhaliev, Kh.S., Krysin, M.Yu., Potapov, A.Yu., Ledenyova, I.V., Kosheleva, Ye.A., and Vandyshev, D.Yu., Chem. Heterocycl. Compd., 2019, vol. 55, p. 748. https://doi.org/10.1007/s10593-019-02530-5

    Article  CAS  Google Scholar 

  27. Vandyshev, D.Y., Shikhaliev, K.S., Kokonova, A.V, Potapov, A.Yu., Kolpakova, M.G., Sabynin, A.L., and Zubkov, F.I., Chem. Heterocycl. Compd., 2016, vol. 52, p. 493. https://doi.org/10.1007/s10593-016-1914-7

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The IR and mass spectra were recorded using the facilities of the Joint Scientific Equipment Center at the Voronezh State University.

Funding

This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation in the framework of state assignment for higher education institutions in the sphere of research activity for 2020–2022 (project no. FZGU-2020-0044).

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Correspondence to Kh. S. Shikhaliev.

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Shmoylova, Y.U., Kovygin, Y.A., Vandyshev, D.Y. et al. Efficient Synthesis of Pyrido[2,3-d]pyrimidines by Recyclization of N-Arylitaconimides with Aminopyrimidinones. Russ J Org Chem 56, 1512–1518 (2020). https://doi.org/10.1134/S107042802009002X

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  • DOI: https://doi.org/10.1134/S107042802009002X

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