Advertisement

Chemistry of Heterocyclic Compounds

, Volume 54, Issue 4, pp 417–427 | Cite as

New chiral proline-based catalysts for silicon and zirconium oxides-promoted asymmetric Biginelli reaction

  • Yulia A. Titova
  • Dmitry A. Gruzdev
  • Olga V. Fedorova
  • Olga A. Alisienok
  • Anna N. Murashkevich
  • Victor P. Krasnov
  • Gennady L. Rusinov
  • Valery N. Charushin
Article
  • 46 Downloads

4-Hydroxy-(2S)-prolines bearing 3,4-dihydro-2H-1,4-benzoxazine or 1,2,3,4-tetrahydroquinoline fragments were synthesized and studied as chiral catalysts in the Biginelli reaction. The target product ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate was obtained with 54% enantiomeric excess (ee). An increase in ee values of the reaction product up to 76% was observed in the presence of nanosized oxides SiO2–ZrO2 as heterogeneous promoters.

Keywords

hydroxyproline silica oxide zirconium oxide asymmetric catalysis Biginelli reaction nanosized oxide 

References

  1. 1.
    (a) Janis, R. A.; Silver, P. J.; Triggle, D. J. Adv. Drug. Res. 1987, 16, 309. (b) Kappe, O. C. Tetrahedron 1993, 49, 6937.Google Scholar
  2. 2.
    (a) Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O'Reelly, B. C. J. Med. Chem. 1991, 34, 806. (b) Kappe, O. C. Eur. J. Med. Chem. 2000, 35, 1043. (c) Triggle, D. J. Cell. Mol. Neurobiol. 2003, 23, 293.Google Scholar
  3. 3.
    Bozsing, D.; Sohar, P.; Gigler, G.; Kovacs, G. Eur. J. Med. Chem. 1996, 31, 663.CrossRefGoogle Scholar
  4. 4.
    (a) Ashok, M.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem. 2007, 42, 380. (b) Ghorab, M. M.; Mohamed, Y. A.; Mohamed, S. A.; Ammar, Y. A. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 108, 249.Google Scholar
  5. 5.
    (a) Shkurko, O. P.; Tolstikova, T. G.; Sedova, V. F. Russ. Chem. Rev. 2016, 85, 1056. (b) Magerramov, A. M.; Kurbanova, M. M.; Abdinbekova, R. T.; Rzaeva, I. A.; Farzaliev, V. M.; Allakhverdiev, M. A. Russ. J. Appl. Chem. 2006, 79, 787. [Zh. Prikl. Khim. 2006, 79, 796.]Google Scholar
  6. 6.
    Kappe, C. O. In Multicomponent Reactions; Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005, p. 109.Google Scholar
  7. 7.
    (a) DeBonis, S.; Simorre, J. P.; Crevel, I.; Lebeau, L.; Skoufias, D. A.; Blangy, A.; Ebel, C.; Gans, P.; Cross, R.; Hackney, D. D.; Wade, R. H.; Kozielski, F. Biochemistry 2003, 42, 338. (b) Maliga, Z.; Kapoor, T. M.; Mitchison, T. J. Chem. Biol. 2002, 9, 989.Google Scholar
  8. 8.
    (a) de Graaff, C.; Ruijter, E.; Orru, R. V. A. Chem. Soc. Rev. 2012, 41, 3969. (b) Heravi, M. M.; Asadi, S.; Lashkariani, B. M. Mol. Diversity 2013, 17, 389. (c) Wan, J.-P.; Lin, Y.; Liu, Y. Curr. Org. Chem. 2014, 18, 687.Google Scholar
  9. 9.
    Fedorova, O. V.; Valova, M. S.; Titova, Yu. A.; Ovchinnikova, I. G.; Grishakov, A. N.; Uimin, M. A.; Mysik, A. A.; Ermakov, A. E.; Rusinov, G. L.; Charushin, V. N. Kinet. Catal. 2011, 52, 226.Google Scholar
  10. 10.
    (a) Mao, J.; Guo, J. Chirality 2010, 22, 173. (b) Watts, J.; Luu, L.; McKee, V.; Carey, E.; Kelleher, F. Adv. Synth. Catal. 2012, 354, 1035. (c) Xin, J.; Chang, L.; Hou, Z.; Shang, D.; Liu, X.; Feng, X. Chem.–Eur. J. 2008, 14, 3177. (d) Yadav, G. D.; Singh, S. Tetrahedron: Asymmetry 2015, 26, 1156.Google Scholar
  11. 11.
    Krivtsov, I. V.; Titova, Yu. A.; Ilkaeva, M. V.; Avdin, V. V.; Fedorova, O. V.; Khainakov, S. A.; Garcia, J. R.; Rusinov, G. L.; Charushin, V. N. J. Sol–Gel Sci. Technol. 2014, 69, 448.Google Scholar
  12. 12.
    Fedorova, O. V.; Titova, Yu. A.; Vigorov, A. Yu.; Toporova, M. S.; Alisienok, O. A.; Murashkevich, A. N.; Krasnov, V. P.; Rusinov, G. L.; Charushin, V. N. Catal. Lett. 2016, 146, 493.Google Scholar
  13. 13.
    Liu, W.-B.; He, H.; Dai, L.-X.; You, S -L. Synthesis 2009, 2076.Google Scholar
  14. 14.
    Pullmann, T.; Engendahl, B.; Zhang, Z.; Hölscher, M.; Zanotti-Gerosa, A.; Dyke, A.; Franciò, G.; Leitner, W. Chem.–Eur. J. 2010, 16, 7517.CrossRefPubMedGoogle Scholar
  15. 15.
    Kesselgruber, M.; Lotz, M.; Martin, P.; Melone, G.; Müller, M.; Pugin, B.; Naud, F.; Spindler, F.; Thommen, M.; Zbiden, P.; Blaser, H. U. Chem.–Asian J. 2008, 3, 1384.CrossRefGoogle Scholar
  16. 16.
    Kündig, E. P.; Meier, P. Helv. Chim. Acta. 1999, 82, 1360.CrossRefGoogle Scholar
  17. 17.
    (a) Charushin, V. N.; Krasnov, V. P.; Levit, G. L.; Korolyova, M. A.; Kodess, M. I.; Chupakhin, O. N.; Kim, M. H.; Lee, H. S.; Park, Y. J.; Kim, K. C. Tetrahedron: Asymmetry 1999, 10, 2691. (b) Gruzdev, D. A.; Levit, G. L.; Krasnov, V. P. Tetrahedron: Asymmetry 2012, 23, 1640. (c) Krasnov, V. P.; Levit, G. L.; Bukrina, I. M.; Andreeva, I. N.; Sadretdinova, L. Sh.; Korolyova, M. A.; Kodess, M. I.; Charushin, V. N.; Chupakhin, O. N. Tetrahedron: Asymmetry 2003, 14, 1985. (d) Gruzdev, D. A.; Levit, G. L.; Kodess, M. I.; Krasnov, V. P. Chem. Heterocycl. Compd. 2012, 48, 748. [Khim. Geterotsikl. Soedin. 2012, 805.]Google Scholar
  18. 18.
    Mori, M.; Uozumi, Y.; Kimura, M.; Ban, Y. Tetrahedron 1986, 42, 3793.CrossRefGoogle Scholar
  19. 19.
    Gruzdev, D. A.; Vakarov, S. A.; Levit, G. L.; Krasnov, V. P. Chem. Heterocycl. Compd. 2014, 49, 1795. [Khim. Geterotsikl. Soedin. 2014, 1936.]Google Scholar
  20. 20.
    Bowers-Nemia, M. M.; Joullié, M. M. Heterocycles 1983, 20, 817.CrossRefGoogle Scholar
  21. 21.
    (a) Kronenthal, D. R.; Mueller, R. H.; Kuester, P. L.; Kissick, T. P.; Johnson, E. J. Tetrahedron Lett. 1990, 31, 1241. (b) Thaning, M.; Wistrand, L. G. Helv. Chim. Acta 1986, 69, 1711.Google Scholar
  22. 22.
    (a) Gómez-Vidal, J. A.; Silverman, R. B. Org. Lett. 2001, 3, 2481. (b) Seo, J.; Martásek, P.; Roman, L. J.; Silverman, R. B. Bioorg. Med. Chem. 2007, 15, 1928.Google Scholar
  23. 23.
    Chorghade, M. S.; Mohapatra, D. K.; Sahoo, G.; Gurjar, M. K.; Mandlecha, M. V.; Bhoite, N.; Moghe, S.; Raines, R. T. J. Fluorine Chem. 2008, 129, 781.CrossRefGoogle Scholar
  24. 24.
    Shiuey, S. J.; Partridge, J. J.; Uskoković, M. R. J. Org. Chem. 1988, 53, 1040.CrossRefGoogle Scholar
  25. 25.
    (a) Kizirian, J.-C. Chem. Rev. 2008, 108, 140. (b) Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580. (c) Terakado, D.; Oriyama, T. Org. Synth. 2006, 83, 70.Google Scholar
  26. 26.
    Amedjkouh, M.; Ahlberg, P. Tetrahedron: Asymmetry 2002, 13, 2229.CrossRefGoogle Scholar
  27. 27.
    (a) Ding, D.; Zhao, C. G. Eur. J. Org. Chem. 2010, 3802. (b) Li, Z. Y.; Xing, H. J.; Huang, G. L.; Sun, X. Q.; Jiang, J. L.; Wang, L. Y. Sci. China: Chem. 2011, 54, 1726.Google Scholar
  28. 28.
    (a) Tanabe, K. Solid Acids and Bases. Their Catalytic Properties; Academic Press: New-York, London, 1970, p. 88. (b) Valova, M. S.; Koryakova, O. V.; Maximovskikh, A. I.; Fedorova, O. V.; Murashkevich, A. N.; Alisienok, O. A. J. Appl. Spectrosc. 2014, 81, 422.Google Scholar
  29. 29.
    (a) Titova, Yu. A.; Fedorova, O. V.; Rusinov, G. L.; Charushin, V. N. Russ. Chem. Rev. 2015, 84, 1294. (b) Fedorova, O. V.; Koryakova, O. V.; Valova, M. S.; Ovchinnikova, I. G.; Titova, Y. A.; Rusinov, G. L.; Charushin, V. N. Kinet. Catal. 2010, 51, 566.Google Scholar
  30. 30.
    Saha, S; Moorthy, J. N. J. Org. Chem. 2011, 76, 396.CrossRefGoogle Scholar
  31. 31.
    Kleidernigg, O. P.; Kappe, O. C. Tetrahedron: Asymmetry 1997, 8, 2057.CrossRefGoogle Scholar
  32. 32.
    Charushin, V. N.; Gorbunov, E. B.; Rusinov, G. L.; Likholobov V. A.; Rodionov, V. A. RU Patent 2434005; Chem. Abstr. 2011, 155, 683753.Google Scholar
  33. 33.
    Asagarasu, A.; Uchiyama, T.; Achiwa, K. Chem. Pharm. Bull. 1998, 46, 697.CrossRefPubMedGoogle Scholar
  34. 34.
    Cassal, J.-M.; Fürst, A.; Meier, W. Helv. Chim. Acta 1976, 59, 1917.CrossRefGoogle Scholar
  35. 35.
    (a) Murashkevich, A. N.; Lavitskaya, A. S.; Barannikova, T. I.; Zharskiy, I. M. J. Appl. Spectr. 2008, 75, 730. [Zh. Prikl. Spectr. 2008, 75, 724.] (b) Murashkevich, A. N.; Alisienok, O. A.; Zharskiy, I. M.; Yukhno, E. K. J. Sol-Gel Sci. Technol. 2013, 68, 509.Google Scholar
  36. 36.
    Liberto, N. A.; Silva, S. P.; de Fátima, A. D.; Fernandes, S. A. Tetrahedron 2013, 69, 8245.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Yulia A. Titova
    • 1
  • Dmitry A. Gruzdev
    • 1
  • Olga V. Fedorova
    • 1
  • Olga A. Alisienok
    • 2
  • Anna N. Murashkevich
    • 2
  • Victor P. Krasnov
    • 1
  • Gennady L. Rusinov
    • 1
    • 3
  • Valery N. Charushin
    • 1
    • 3
  1. 1.Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesYekaterinburgRussia
  2. 2.Belarusian State Technical UniversityMinskBelarus
  3. 3.Ural Federal University named after the First President of Russia B. N. YeltsinYekaterinburgRussia

Personalised recommendations