Synthesis of substituted cyclohexenones by reaction of chalcones with acetoacetic acid amides

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Abstract

New 4-aryl-2-oxo-6-phenyl-3-cyclohexene-1-carboxamides were obtained by the reaction of N -substituted acetoacetic acid amides with benzalacetophenone and 4-methoxybenzalacetophenone in alcohol in the presence of potassium hydroxide. Structure of the prepared compounds was proved using IR, 1H and 13C NMR spectroscopy, mass spectrometry and X-rays analysis data.

About the authors

N. V. Nosova

Perm State Pharmaceutical Academy

A. A. Sokolov

Perm State Pharmaceutical Academy

V. L. Gein

Perm State Pharmaceutical Academy

Email: geinvl48@mail.ru

M. V. Dmitriev

Perm State National Research University

I. G. Mokrushin

Perm State National Research University

References

  1. Prado S., Li Y., Nay B. // Stud. Nat. Prod. Chem. 2012. Vol. 36. P. 249. doi: 10.1016/B978-0-444-53836-9.00025-6
  2. Wisetsai A., Lekphrom R., Schevenels F.T. // Nat. Prod. Res. 2018. Vol. 32. N 21. P. 2499. doi: 10.1080/14786419.2017.1423299
  3. Mayekar A.N., Li H., Yathirajan H., Narayana B., Kumari N.S. // Int. J. Chem. 2010. Vol. 2. N 2. P. 114. doi: 10.5539/ijc.v2n2p114
  4. Abdel-Galil E., Girges M.M., Said G.E. // Russ. J. Gen. Chem. 2022. Vol. 92. N 10. P. 2169. doi: 10.1134/S1070363222100292
  5. Khan J., Ali G., Rashid U., Khan R., Jan M.S., Ullah R., Ahmad S., Abbasi S. W., Atif Ali Khan Khalil, Robert D.E. Sewell // Eur. J. Pharmacol. 2021. Vol. 902. Art. 174091. doi: 10.1016/j.ejphar.2021.174091
  6. Vyas D.H., Tala S.D., Akbari J.D., Dhaduk M.F., Joshi H.S. // Indian J. Chem. (B). 2009. Vol. 48B. P. 1405.
  7. Shin S.Y., Park J., Jung Y., Lee H.Y., Koh D., Yoon Y., Lim Y. // Appl. Biolog. Chem. 2020. Vol. 63. Art. 82. doi: 10.1186/s13765-020-00567-1
  8. Wen Z.-K., Wu X.-X., Bao W.-K., Xiao J.-J., Chao J.-B. // Org. Lett. 2020. Vol. 22. N 12. P. 4898. doi: 10.1021/acs.orglett.0c01763
  9. Odiya S.P., Das S.P., Boruah J.J., Rajani D.P. // Russ. J. Org. Chem. 2023. Vol. 59. P. 117. doi: 10.1134/S107042802301013X
  10. Hazeri N., Kangani M. // Polycycl. Arom. Compd. 2018. Vol. 40. N 5. P. 1479. doi: 10.1080/10406638.2018.1557706
  11. Badshah A., Nawaz S., Nazar M.F., Shah. S.S., Hasan A. // J. Fluor. 2010. Vol. 20. P. 1049. doi: 10.1007/s10895-010-0657-6
  12. Winter N., Trauner D. // Beilstein J. Org. Chem. 2019. Vol. 15. P. 2271. doi: 10.3762/bjoc.15.219
  13. Stierle D.B., Stierle A.A., Bungi T. // J. Org. Chem. 2003. Vol. 68. N 12. P. 4966. doi: 10.1021/jo0340253
  14. Li J.Y., Harper. J.K., Grant D.M., Tombe B.O., Bashyal B., Hess W.M., Strobel G.A. // Phytochemistry. 2001. Vol. 56. N 5. P. 463. doi: 10.1016/S0031-9422(00)00408-8
  15. Hayden F.G., Gubareva L.V., Monto A.S., Klein T.C., Elliott M.J., Hammond J.M., Sharp S.J., Ossi M.J. // N. Engl. J. Med. 2000. Vol. 343. P. 1282. doi: 10.1056/NEJM200011023431801
  16. Marcial B.L., Sousa S.F., Santos H.F. Dos, Ramos M.J. // J. Biomol. Struct. Dyn. 2014. Vol. 32. N 12. P. 1907. doi: 10.1080/07391102.2013.842186
  17. Aris P., Wei Y., Mohamadzadeh M., Xia X. // Molecules. 2022. Vol. 27. N 20. P. 7034. doi: 10.3390/molecules27207034
  18. Гейн В.Л., Вагапов А.В., Носова Н.В., Воронина Э.В., Вахрин М.И., Кривенко А.П. // Хим.-фарм. ж. 2010. Т. 44. № 5. С. 13
  19. Gein V.L., Vagapov A.V., Nosova N.V., Voronina E.V., Vahrin M.I., Krivenko A.P. // Pharm. Chem. J. 2010. Vol. 44. N 5. P. 245. doi: 10.1007/s11094-010-0440-7
  20. Носова Н.В., Соколов А.А., Гейн О.Н., Гейн В.Л., Янкин А.Н., Данилов С.Е., Дмитриев М.В. // ЖОХ. Т. 90. № 9. С. 1315
  21. Nosova N.V., Sokolov A.A., Gein O.N., Gein V.L., Yankin A.N., Danilov S.E., Dmitriev M.V. // Russ. J. Gen. Chem. 2020. Vol. 90. N 9. P. 1315. doi: 10.31857/S0044460X20090012
  22. Гейн В.Л., Вагапов А.В., Носова Н.В., Воронина Э.В., Вахрин М.И., Кривенко А.П. // Хим.-фарм. ж. 2010. Т. 44. № 5. С. 1
  23. Gein V.L., Vagapov A.V., Nosova N.V., Voronina E.V., Vahrin M.I., Krivenko A.P. // Pharm. Chem. J. 2010. Vol. 44. N 5. P. 245. doi: 10.1007/s11094-010-0440-7
  24. CrysAlisPro, Agilent Technologies, Version 1.171.37.33.
  25. Sheldrick G.M. // Acta Crystallogr. (A). 2015. Vol. 71. P. 3. doi: 10.1107/S2053273314026370

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