Synthesis of novel tetrahydropyrimidines via the reaction of sodium [1-(3,3-diethoxypropyl)ureido]methansulfonates 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]methansulfonates with various C -nucleophiles (4-chlororesorcinol, sesamol, 2,4-dihydroxybenzoic acid, 4-hydroxy-6-methyl-2 H -pyran-2-one) in chloroform in the presence of trifluoroacetic acid.

About the authors

A. V Smolobochkin

Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”

Email: smolobochkin@iopc.ru

L. J Yakhshilikova

Kazan National Research Technological University

T. S Rizbayeva

Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”

A. S Gazizov

Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”

A. R Burilov

Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”

M. A Pudovik

Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”

References

  1. Смолобочкин А.В., Газизов А.С., Бурилов А.Р., Пудовик М.А., Синяшин О.Г. // Усп. хим. 2021. Т. 90. С. 395
  2. Smolobochkin A.V., Gazizov A.S., Burilov A.R., Pudovik M.A., Sinyashin O.G. // Russ. Chem. Rev. 2021. Vol. 90. P. 395. doi: 10.1070/RCR4988
  3. De Lucca G.V., Liang J., De Lucca I. // J. Med. Chem. 1999. Vol. 42. P. 135. doi: 10.1021/jm9803626
  4. Katritzky A.R., Oliferenko A., Lomaka A., Karelson M. // Bioorg. Med. Chem. Lett. 2002. Vol. 12. P. 3453. doi: 10.1016/S0960-894X(02)00741-2
  5. Adams J.L., Meek T.D., Mong S.M., Johnson R.K., Metcalf B.W. // J. Med. Chem. 1988. Vol. 31. P. 1355. doi: 10.1021/jm00402a018
  6. Zhu L., Cheng P., Lei N., Yao J., Sheng C., Zhuang C., Guo W., Liu W., Zhang Y., Dong G., Wang S., Miao Z., Zhang W. // Arch. Pharm. 2011. Vol. 344. P. 726. doi: 10.1002/ardp.201000402
  7. Das Gupta S., Murumkar P.R., Giridhar R., Yadav M.R. // Bioorg. Med. Chem. 2009. Vol. 17. P. 3604. doi: 10.1016/j.bmc.2009.04.003
  8. Yoshimitsu T., Arano Y., Nagaoka H. // J. Am. Chem. Soc. 2005. Vol. 127. P. 11610. doi: 10.1021/ja053855q
  9. Hori M., Sakakura A., Ishihara K. // J. Am. Chem. Soc. 2014. Vol. 136. P. 13198. doi: 10.1021/ja508441t
  10. Guyonnet M., Baudoin O. // Org. Lett. 2012. Vol. 14. P. 398. doi: 10.1021/ol2031763
  11. Смолобочкин А.В., Газизов А.С., Бурилов А.Р., Пудовик М.А., Синяшин О.Г. // Усп. хим. 2019. Т. 88. С. 1104
  12. Smolobochkin A.V., Gazizov A.S., Burilov A.R., Pudovik M.A., Sinyashin O.G. // Russ. Chem. Rev. 2019. Vol. 88. P. 1104. doi: 10.1070/RCR4891
  13. Primo A., Aguado E., Garcia H. // ChemCatChem. 2013. Vol. 5. P. 1020. doi: 10.1002/cctc.201200329
  14. 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., Willis E. // Bioorg. Med. Chem. Lett. 2018. Vol. 28. P. 293. doi: 10.1016/j.bmcl.2017.12.051
  15. Taily I.M., Saha D., Banerjee P. // Eur. J. Org. Chem. 2019. P. 7804. doi: 10.1002/ejoc.201901400
  16. He Z., Zhou Q., Wu L., Chen Y. // Adv. Synth. Catal. 2010. Vol. 352. P. 1904. doi: 10.1002/adsc.201000291
  17. Wu T., Cheng J., Chen P., Liu G. // Chem. Commun. 2013. Vol. 49. P. 8707. doi: 10.1039/c3cc44711a
  18. Smolobochkin A. V., Gazizov A.S., Voronina J.K., Strelnik A.G., Rizbayeva T.S., Burilov A.R., Pudovik M.A. // ChemistrySelect. 2019. Vol. 4. P. 11038. doi: 10.1002/slct.201902754
  19. Taylor H.M., Hauser C.R. // Org. Synth. 1963. Vol. 43. P. 25. doi: 10.15227/orgsyn.043.0025
  20. Molodtsov V., Fleming P.R., Eyermann C.J., Ferguson A.D., Foulk M.A., McKinney D.C., Masse C.E., Buurman E.T., Murakami K.S. // J. Med. Chem. 2015. Vol. 58. P. 3156. doi: 10.1021/acs.jmedchem.5b00050
  21. Cook L., Ternai B., Ghosh P. // J. Med. Chem. 1987. Vol. 30. P. 1017. doi: 10.1021/jm00389a010
  22. Fang Z., Liao P.-C., Yang Y.-L., Yang F.-L., Chen Y.-L., Lam Y., Hua K.-F., Wu S.-H. // J. Med. Chem. 2010. Vol. 53. P. 7967. doi: 10.1021/jm100619x

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