Russian Journal of General Chemistry

, Volume 86, Issue 12, pp 2837–2844 | Cite as

Lewis acid-promoted direct synthesis of N-unsubstituted hydrazones via the reaction of hydrazine with acetophenone and isatin derivatives

  • A. S. El-AzabEmail author
  • H. A. Ghabbour
  • W. M. El-Husseiny
  • A. R. Maarouf
  • M. A. Mohamed
  • A. A.-M. Abdel-Aziz


Hydrazones 2–22 were synthesized via the reaction of acetophenone with isatin derivatives and anhydrous hydrazine promoted by BF3 as a Lewis acid at 0°C. Structures of the synthesized hydrazones were determined on the basis of NMR and X-ray crystallographic analyses.


efficient method N-unsubstituted hydrazone Lewis acids BF3 X-ray crystal structure 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1. (a)
    Todeschini, A.R., Miranda, A.L., Silva, C.M., Parrini, S.C., and Barreiro, E., J. Eur. J. Med. Chem., 1998, vol. 33, p. 189 doi 10.1016/S0223-5234(98)80008-1CrossRefGoogle Scholar
  2. (b).
    Gemma, S., Kukreja, G., Fattorusso, C., Persico, M., Romano, M., Altarelli, M., Savini, L., Campiani, G., Fattorusso, E., and Basilico, N., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 5384. doi 10.1016/j.bmcl.2006.07.060CrossRefGoogle Scholar
  3. (c).
    Savini L., Chiasserini, L., Gaeta, A., and Pellerano, C., Bioorg. Med. Chem., 2002, vol. 10, p. 2193. doi 10.1016/S0968-0896(02)00071-8CrossRefGoogle Scholar
  4. (d).
    Zarghi, A., Tahghighi, A., Soleimani, Z., Daraie, B., Dadrass, O.G., and Hedayati, M., Sci Pharm., 2008, vol. 76, p. 361. doi 10.3797/scipharm.0805-20CrossRefGoogle Scholar
  5. (e).
    Jadhav, S.Y., Shirame, S.P., Kulkarni, S.D., Patil, S.B., Pasale, S.K., and Bhosale, R.B., Bioorg Med. Chem. Lett., 2013, vol. 23, p. 2575. doi 10.1016/j.bmcl.2013.02.105CrossRefGoogle Scholar
  6. (f).
    Bansal, S., Bala, M., Suthar, S.K., Choudhary, S., Bhattacharya, S., Bhardwaj, V., Singla, S., and Joseph, A., Eur. J. Med. Chem., 2014, vol. 80, p. 167. doi 10.1016/j.ejmech.2014.04.045CrossRefGoogle Scholar
  7. (g).
    Xing, M., Zhao, T.-T., Ren, Y.-J., Peng, N.-N., Yang, X.-H., Li, X., Zhang, H., Liu, G.-Q., Zhang, L.-R., and Zhu, H.-L., Med. Chem. Res., 2014, vol. 23, p. 3274. doi 10.1007/s00044-014-0909-0CrossRefGoogle Scholar
  8. (h).
    Verma, G., Marella, A., Shaquiquzzaman, M., Akhtar, M., Ali, M.R., and Alam, M.M., J. Pharm. Bioallied. Sci., 2014, vol. 6, p. 69. doi 10.4103/0975-7406.129170CrossRefGoogle Scholar
  9. 2. (a)
    Kleine, T., Fröhlich, R., Wibbeling, B., and Würthwein, E.-U., J. Org. Chem., 2011, vol. 76, p. 4591. doi 10.1021/jo200487vCrossRefGoogle Scholar
  10. (b).
    Perdicchia, D., Licandro, E., Maiorana, S., Baldolib C., and Gianninia, C., Tetrahedron, 2003, vol. 59, p. 7733. doi 10.1016/S0040- 4020(03)01208-0CrossRefGoogle Scholar
  11. (c).
    Patrick, T.B. and Flory, P.A., J. Fluorine Chem., 1984, vol. 25, p. 157. doi 10.1016/S0022-1139(00)80945-8CrossRefGoogle Scholar
  12. (d).
    Baruah, B., Dutta, M.P., Boruah, A., Prajapati, D., and Sandhu, J.S., Synlett, 1999, vol. 4, p. 409. doi 10.1055/s-1999-2637CrossRefGoogle Scholar
  13. (e).
    Wu, P.-L., Peng, S.-Y., and Magrath, J., Synthesis, 1995, vol. 4, p. 435. doi 10.1055/s-1995-3932CrossRefGoogle Scholar
  14. (f).
    Ghali, N.I., Venton, D.L., Hung, S.C., and Le Breton, G.C., J. Org. Chem., 1981, vol. 46, p. 5413. doi 10.1021/jo00339a035CrossRefGoogle Scholar
  15. (g).
    Kabalka, G.W., Baker J.D., and Neal, G.W., J. Org. Chem., 1977, vol. 42, p. 512. doi 10.1021/jo00423a025CrossRefGoogle Scholar
  16. (h).
    Riepl, H.M. and Kellermann, M., Helv. Chim. Acta, 2009, vol. 92, p. 668. doi 10.1002/hlca.200800337CrossRefGoogle Scholar
  17. 3.
    Manzano, R., Wurm, T., Frank Rominger, F., and Hashmi, A.S.K., Chem. Eur. J., 2014, vol. 20, p. 6844. doi 10.1002/anie.201209618CrossRefGoogle Scholar
  18. 4.
    Zhang, G., Zhao, Y., and Ge, H., Angew. Chem. Int. Ed., 2013, vol. 52, p. 2559. doi 10.1021/jo01341a008CrossRefGoogle Scholar
  19. 5.
    Newkome, G.R. and Fishel, D.L., J. Org. Chem., 1966, vol. 31, p. 677.CrossRefGoogle Scholar
  20. 6.
    Barton, D.H.R., O’Brien, R.E., and Sternhell, S., J. Chem. Soc., 1962, p. 470. doi 10.1039/JR9620000470Google Scholar
  21. 7.
    Lock, G. and Stach, K., Ber., 1944, vol. 77, p. 293. doi 10.1002/cber.19440770503 8.Google Scholar
  22. (a).
    Hayashi, S., Ueno, N., Murase, A., and Takada, J., J. Enzyme Inhib. Med. Chem., 2014, vol. 29, p. 846. doi 10.3109/14756366.2013.864650CrossRefGoogle Scholar
  23. (b).
    Cheng-Chu Z., Xue-Mei, L., Hong, Y., and Ru-Gang, Z., Chin. J. Chem., 2007, vol. 25, p. 1174. doi 10.1002/cjoc.200790219 9.CrossRefGoogle Scholar
  24. (a).
    Singh, G.S. and Desta, Z.Y., Chem. Rev., 2012, vol. 112, p. 6104CrossRefGoogle Scholar
  25. (b).
    Kidwai, M., Jahan, A., and Mishra, N.K., Med. Chem., 2014, vol. 4, p. 451. doi 10.1021/cr300135yCrossRefGoogle Scholar
  26. 10.
    Coffey, K.E., Moreira, R., Abbas, F.Z., and Murphy, G.K., Org. Biomol. Chem., 2015, vol. 13, p. 682. doi 10.1039/c4ob02213kCrossRefGoogle Scholar
  27. 11.
    Sheldrick, G.M., Acta Crystallogr. A, 2008, vol. 64, p. 112. doi 10.1107/S0108767307043930CrossRefGoogle Scholar
  28. 12.
    Bruker. SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA, 2012.Google Scholar
  29. 13.
    HyperChem, Version 5.1; Hypercube.Google Scholar
  30. 14.
    Profeta, S. and Allinger, N.L., J. Am. Chem. Soc., 1985, vol. 107, p. 1907. doi 10.1021/ja00293a019CrossRefGoogle Scholar
  31. 15.
    Stewart, J.J.P., J. Comput. Chem., 1989, vol. 10, p. 209. doi 10.1002/jcc.540100208CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • A. S. El-Azab
    • 1
    • 2
    Email author
  • H. A. Ghabbour
    • 1
    • 3
  • W. M. El-Husseiny
    • 4
  • A. R. Maarouf
    • 3
    • 5
  • M. A. Mohamed
    • 2
    • 6
  • A. A.-M. Abdel-Aziz
    • 1
    • 3
  1. 1.Department of Pharmaceutical Chemistry, College of PharmacyKing Saud UniversityRiyadhSaudi Arabia
  2. 2.Department of Organic Chemistry, Faculty of PharmacyAl-Azhar UniversityCairoEgypt
  3. 3.Department of Medicinal Chemistry, Faculty of PharmacyMansoura UniversityMansouraEgypt
  4. 4.Department of Pharmaceutical Organic Chemistry, Faculty of PharmacyMansoura UniversityMansouraEgypt
  5. 5.Department of Pharmaceutical Chemistry, College of PharmacyDelta University for Science and TechnologyGamasa CityEgypt
  6. 6.Department of Pharmaceutical Chemistry, College of PharmacyPrince Sattam Bin Abdulaziz UniversityAlKharjSaudi Arabia

Personalised recommendations