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Biginelli Reaction in the Synthesis of Ethyl 4-(6-Aryl-5-benzoyl-4-hydroxy-2-thioxohexahydropyrimidine-4-carboxamido)benzoates

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Abstract

Three-component Biginelli reaction of ethyl 4-(2,4-dioxo-4-phenylbutanamido)benzoate, aromatic aldehyde and thiourea in acetic acid in the presence of sodium acetate led to the formation of ethyl 4-(6-aryl-5-benzoyl-4-hydroxy-2-thioxohexahydropyrimidine-4-carboxamido)benzoates. Structure of the obtained compounds was established by IR, 1H NMR, 13C spectroscopy methods.

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REFERENCES

  1. Kappe, C.O., Multicomponent Reactions, 2005, p. 95. https://doi.org/10.1002/3527605118.ch4

  2. Kappe, C.O., Tetrahedron, 1993, vol. 49, no. 32, p. 6937. https://doi.org/10.1016/S0040-4020(01)87971-0

    Article  CAS  Google Scholar 

  3. Kappe, C.O., Eur. J. Med. Chem., 2000, vol. 35, no. 12, p. 1043. https://doi.org/10.1016/s0223-5234(00)01189-2

    Article  CAS  PubMed  Google Scholar 

  4. Wan, J.-P. and Liu, Y., Synthesis, 2010, no. 23, p. 3943. https://doi.org/10.1055/s-0030-1258290

    Article  CAS  Google Scholar 

  5. Nagarajaiah, H., Mukhopadhyay, A., and Moorthy, J.N., Tetrahedron Lett., 2016. 57, no. 47, p. 5135. https://doi.org/10.1016/j.tetlet.2016.09.047

    Article  CAS  Google Scholar 

  6. Vdovina, S.V. and Mamedov, V.A., Russ. Chem. Rev., 2008, vol. 77, p. 1017. https://doi.org/10.1070/RC2008v077n12ABEH003894

    Article  CAS  Google Scholar 

  7. Gein, V.L., Krylova, I.V., Tsypliakova, E.P., Gaifullina, A.R., Varkentin, L.I., and Vakhrin, M.I., Chem. Heterocycl. Compd., 2009, vol. 45, no. 7, p. 829. https://doi.org/10.1007/S10593-009-0353-0

    Article  CAS  Google Scholar 

  8. Gein, V.L., Zamaraeva, T.M., Gorgopina, E.V., and Dmitriev, M.V., Chem. Heterocycl. Compd., 2020, vol. 56, no. 3, p. 339. https://doi.org/10.1007/s10593-020-02665-w

    Article  CAS  Google Scholar 

  9. Zohdi, H.F., Rateb, N.M., and Elnagdy, S.M., Eur. J. Med. Chem., 2011, vol. 46, no. 11, p. 5636. https://doi.org/10.1016/j.ejmech.2011.09.036

    Article  CAS  PubMed  Google Scholar 

  10. Ryabukhin, S.V., Plaskon, A.S., Bondarenko, S.S., Ostapchuk, E.N., Grygorenko, O.O., Shishkin, O.V., and Tolmachev, A.A., Tetrahedron Lett., 2010, vol. 51, no. 32, p. 4229. https://doi.org/10.1016/j.tetlet.2010.06.032

    Article  CAS  Google Scholar 

  11. El-Malah, A., Mahmoud, Z., Hamed Salem, H., Abdou, A.M., Soliman Mona, M.H., and Hassan, R.A., Green Chem. Lett. Rev., 2021, vol. 14, no. 2, p. 2. https://doi.org/10.1080/17518253.2021.1896789

    Article  CAS  Google Scholar 

  12. Lauro, G., Strocchia, M., Terracciano, S., Bruno, I., Fischer, K., Pergola, C., Werz, O., Riccio, R., and Bifulco, G., Eur. J. Med. Chem., 2014, vol. 80, p. 407. https://doi.org/10.1016/j.ejmech.2014.04.061

    Article  CAS  PubMed  Google Scholar 

  13. Kolosov, M.A., Al-Ogaili, M.J.K., Parkhomenko, V.S., and Orlov, V.D., Chem. Heterocycl. Compd., 2014, vol. 49, no. 10, p. 1484. https://doi.org/10.1007/s10593-014-1399-1

    Article  CAS  Google Scholar 

  14. Gein, V.L., Zamaraeva, T.M., Volkova, E.S., and Dmitriev, M.V., Russ. J. Org. Chem., 2016, vol. 52, p. 730. https://doi.org/10.1134/S1070428016050195

    Article  CAS  Google Scholar 

  15. CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171.NET)

  16. Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  PubMed  Google Scholar 

  17. Sheldrick, G.M., Acta Crystallogr. (C), 2015, vol. 71, no. 1, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

  18. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, no. 2, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

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Funding

This work was financially supported by the Perm Scientific and Educational Center “Rational Subsoil Use,” 2022.

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Correspondence to V. L. Gein.

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Gein, V.L., Zamaraeva, T.M., Gorgopina, E.V. et al. Biginelli Reaction in the Synthesis of Ethyl 4-(6-Aryl-5-benzoyl-4-hydroxy-2-thioxohexahydropyrimidine-4-carboxamido)benzoates. Russ J Gen Chem 93, 16–21 (2023). https://doi.org/10.1134/S1070363223010036

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