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Synthesis of Novel Tetrahydropyrimidines via the Reaction of Sodium [1-(3,3-Diethoxypropyl)ureido]methanesulfonates with C-Nucleophiles

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Abstract

A series of new substituted tetrahydropyrimidines was obtained by the reaction of sodium [1-(3,3-diethoxypropyl)ureido]methanesulfonates with various C-nucleophiles (4-chlororesorcinol, sesamol, 2,4-dihydroxybenzoic acid, 4-hydroxy-6-methyl-2H-pyran-2-one) in chloroform in the presence of trifluoroacetic acid.

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REFERENCES

  1. Smolobochkin, A.V., Gazizov, A.S., Burilov, A.R., Pudovik, M.A., and Sinyashin, O.G., Russ. Chem. Rev., 2021, vol. 90, p. 395. https://doi.org/10.1070/RCR4988

    Article  CAS  Google Scholar 

  2. De Lucca, G.V., Liang, J., and De Lucca, I., J. Med. Chem., 1999, vol. 42, p. 135. https://doi.org/10.1021/jm9803626

    Article  CAS  PubMed  Google Scholar 

  3. Katritzky, A.R., Oliferenko, A., Lomaka, A., and Karelson, M., Bioorg. Med. Chem. Lett., 2002, vol. 12, p. 3453. https://doi.org/10.1016/S0960-894X(02)00741-2

    Article  CAS  PubMed  Google Scholar 

  4. Adams, J.L., Meek, T.D., Mong, S.M., Johnson, R.K., and Metcalf, B.W., J. Med. Chem., 1988, vol. 31, p. 1355. https://doi.org/10.1021/jm00402a018

    Article  CAS  PubMed  Google Scholar 

  5. Zhu, L., Cheng, P., Lei, N., Yao, J., Sheng, C., Zhuang, C., Guo, W., Liu, W., Zhang, Y., Dong, G., Wang, S., Miao, Z., and Zhang, W., Arch. Pharm., 2011, vol. 344, p. 726. https://doi.org/10.1002/ardp.201000402

    Article  CAS  Google Scholar 

  6. Das Gupta, S., Murumkar, P.R., Giridhar, R., and Yadav, M.R., Bioorg. Med. Chem., 2009, vol. 17, p. 3604. https://doi.org/10.1016/j.bmc.2009.04.003

    Article  CAS  PubMed  Google Scholar 

  7. Yoshimitsu, T., Arano, Y., and Nagaoka, H., J. Am. Chem. Soc., 2005, vol. 127, p. 11610. https://doi.org/10.1021/ja053855q

    Article  CAS  PubMed  Google Scholar 

  8. Hori, M., Sakakura, A., and Ishihara, K., J. Am. Chem. Soc., 2014, vol. 136, p. 13198. https://doi.org/10.1021/ja508441t

    Article  CAS  PubMed  Google Scholar 

  9. Guyonnet, M. and Baudoin, O., Org. Lett., 2012, vol. 14, p. 398. https://doi.org/10.1021/ol2031763

    Article  CAS  PubMed  Google Scholar 

  10. Smolobochkin, A.V., Gazizov, A.S., Burilov, A.R., Pudovik, M.A., and Sinyashin, O.G., Russ. Chem. Rev., 2019, vol. 88, p. 1104. https://doi.org/10.1070/RCR4891

    Article  CAS  Google Scholar 

  11. Primo, A., Aguado, E., and Garcia, H., ChemCatChem, 2013, vol. 5, p. 1020. https://doi.org/10.1002/cctc.201200329

    Article  CAS  Google Scholar 

  12. Humphries, P.S., Bersot, R., Kincaid, J., Mabery, E., McCluskie, K., Park, T., Renner, T., Riegler, E., Steinfeld, T., Turtle, E.D., Wei, Z.-L., and Willis, E., Bioorg. Med. Chem. Lett., 2018, vol. 28, p. 293. https://doi.org/10.1016/j.bmcl.2017.12.051

    Article  CAS  PubMed  Google Scholar 

  13. Taily, I.M., Saha, D., and Banerjee, P., Eur. J. Org. Chem., 2019, p. 7804. https://doi.org/10.1002/ejoc.201901400

  14. He, Z., Zhou, Q., Wu, L., and Chen, Y., Adv. Synth. Catal., 2010, vol. 352, p. 1904. https://doi.org/10.1002/adsc.201000291

    Article  CAS  Google Scholar 

  15. Wu, T., Cheng, J., Chen, P., and Liu, G., Chem. Commun., 2013, vol. 49, p. 8707. https://doi.org/10.1039/c3cc44711a

    Article  CAS  Google Scholar 

  16. Smolobochkin, A.V., Gazizov, A.S., Voronina, J.K., Strelnik, A.G., Rizbayeva, T.S., Burilov, A.R., and Pudovik, M.A., ChemistrySelect, 2019, vol. 4, p. 11038. https://doi.org/10.1002/slct.201902754

    Article  CAS  Google Scholar 

  17. Taylor, H.M. and Hauser, C.R., Org. Synth., 1963, vol. 43, p. 25. https://doi.org/10.15227/orgsyn.043.0025

    Article  CAS  Google Scholar 

  18. Molodtsov, V., Fleming, P.R., Eyermann, C.J., Ferguson, A.D., Foulk, M.A., McKinney, D.C., Masse, C.E., Buurman, E.T., and Murakami, K.S., J. Med. Chem., 2015, vol. 58, p. 3156. https://doi.org/10.1021/acs.jmedchem.5b00050

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Cook, L., Ternai, B., and Ghosh, P., J. Med. Chem., 1987, vol. 30, p. 1017. https://doi.org/10.1021/jm00389a010

    Article  CAS  PubMed  Google Scholar 

  20. Fang, Z., Liao, P.-C., Yang, Y.-L., Yang, F.-L., Chen, Y.-L., Lam, Y., Hua, K.-F., and Wu, S.-H., J. Med. Chem., 2010, vol. 53, p. 7967. https://doi.org/10.1021/jm100619x

    Article  CAS  PubMed  Google Scholar 

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ACKNOWLEDGMENTS

The authors are grateful to the Spectro-Analytical Center of the Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences” for the technical support.

Funding

This work financially supported by Council for Grants of the President of the Russian Federation for young Russian scientists—candidates of sciences (grant no. MK-1944.2022.1.3).

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Correspondence to A. V. Smolobochkin.

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A.R. Burilov is a member of the editorial board of the Russian Journal of General Chemistry. The other authors declare no conflicts of interest.

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Smolobochkin, A.V., Yakhshilikova, L.J., Rizbayeva, T.S. et al. Synthesis of Novel Tetrahydropyrimidines via the Reaction of Sodium [1-(3,3-Diethoxypropyl)ureido]methanesulfonates with C-Nucleophiles. Russ J Gen Chem 93, 495–499 (2023). https://doi.org/10.1134/S1070363223030052

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