Skip to main content
Log in

One-pot three components synthesis of novel 2-iminoquinazolines and 2-imino spiro[indoline-quinazoline/pyrimidine]ones catalyzed by sodium fluoride

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Sodium fluoride was determined to be an inexpensive, mild and efficient catalyst in the synthesis of 2-iminoquinazoline and spiro indolinepyrimido[4,5-d]pyrimidine derivatives via a three component Biginelli-like reaction of cyclo-β-diketones, aromatic aldehydes or isatin derivatives with guanidine hydrochloride.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Dawei, M. and Qian, C.,. Acc. Chem. Res., 2008, vol. 41, p. 1450.

    Article  Google Scholar 

  2. Monnier, F. and Taillefer, M., Angew. Chem. Int. Ed., 2009, vol. 48, p. 6954.

    Article  CAS  Google Scholar 

  3. Chen, Y., Xie, X., and Ma, D., J. Org. Chem., 2007, vol. 72, p. 9329.

    Article  CAS  Google Scholar 

  4. Wang, B., Lu, B., Jiang, Y., Zhang, Y., and Ma, D., Org. Lett., 2008, vol. 10, p. 2761.

    Article  CAS  Google Scholar 

  5. Truong, V.L., and Morrow, M., Tetrahedron Lett., 2010, vol. 51, p. 758.

    Article  CAS  Google Scholar 

  6. Yang, D. and Fu, H., Chem. Eur. J., 2010, vol. 16, p. 2366.

    Article  CAS  Google Scholar 

  7. Li, X., Yang, D., Jiang, Y., and Fu, H., Green Chem., 2010, vol. 12, p. 1097.

    Article  CAS  Google Scholar 

  8. Rao, H., Fu, H., Yuyang, J., and Zhao, Y., Adv. Synth. Catal., 2010, vol. 352, p. 458.

    Article  CAS  Google Scholar 

  9. Lu, J., Gong, X., Yang, H., and Fu, H., Chem. Commun., 2010, vol. 46, p. 4172.

    Article  CAS  Google Scholar 

  10. Zhao, H., Fu, H., and Qiao, R., J. Org. Chem., 2010, vol. 75, p. 3311.

    Article  CAS  Google Scholar 

  11. Yang, X., Fu, H., Qiao, R., Jiang, Y., and Zhao, Y., Adv. Synth. Catal., 2010, vol. 352, p. 1033.

    Article  CAS  Google Scholar 

  12. Cai, Q., Zou, B., and Ma, D., Angew. Chem. Int. Ed., 2006, vol. 45, p. 1276.

    Article  CAS  Google Scholar 

  13. Kidwai, M., Saxena, S., Khalilur Rahman Khan, M., and Thukral, S.S., Eur. J. Med. Chem., 2005, vol. 40, p. 816.

    Article  CAS  Google Scholar 

  14. Yarim, M., Sarac, S., Kilic, F.S., and Erol, K., IL Farmaco., 2003, vol. 58, p. 17.

    Article  CAS  Google Scholar 

  15. Khurana, J.M. and Kumar, S., Monatsh Chem., 2010, vol. 141, p. 561.

    Article  CAS  Google Scholar 

  16. Lin, H., Zhao, Q., Xu, B., and Wang, X., J. Mol. Catal. A: Chem., 2007, vol. 268, p. 221.

    Article  CAS  Google Scholar 

  17. Hassani, Z., Islami, M.R., and Kalantari, M., Bio. Med. Chem. Lett., 2006, vol. 16, p. 4479l.

    Article  CAS  Google Scholar 

  18. Niralwad, K.S., Shingate, B.B., and Shingare, M.S., Tetrahedron Lett., 2010, vol. 51, p. 3616.

    Article  CAS  Google Scholar 

  19. Maradur, S.P. and Gokavi, G.S., Catal. Commun., 2007, vol. 8, p. 279.

    Article  CAS  Google Scholar 

  20. Heravi, M.M., Bakhtiari, K., and Bamoharram, F.F., Catal. Commun., 2006, vol. 7, p. 373.

    Article  CAS  Google Scholar 

  21. Kumar, A. and Maurya, R. ATetrahedron Lett., 2007, vol. 48, p. 4569.

    Article  CAS  Google Scholar 

  22. Niralwad, K.S., Shingate, B.B., and Shingare, M.S., J. Chin. Chem. Soc., 2010, vol 57, p. 89.

    Article  CAS  Google Scholar 

  23. Khurana, J.M. and Kumar, S., Monatsh Chem., 2010, vol. 141, p. 561.

    Article  CAS  Google Scholar 

  24. Ladani, N.K., Petel, M.P., and Petel, R.G., Arkivoc., 2009, vol. 7, p. 292.

    Article  Google Scholar 

  25. Potapov, A.Yu., Shikhaliev, Kh.S., Krylsky, D.V., and Krisin, M.Yu., Chem. Het. Comp., 2006, vol. 42, p. 1338.

    Article  CAS  Google Scholar 

  26. Dawoud, N.T.A., Chem. Sci. Trans., 2013, vol. 2, p. 129.

    Article  Google Scholar 

  27. Kefayati, H., Rad-Moghadam, K., Zamani, M., and Hosseyni, S., Lett. Org. Chem., 2010, vol. 7, p. 277.

    Article  CAS  Google Scholar 

  28. Kefatati, H., Asghari, F., and Khanjanian, R., J. Mol. Liq., 2012, vol. 172, p. 147.

    Article  Google Scholar 

  29. Kefayati, H., Fakhriyannejad, M., Mohammadi, A.A., Phosph. Sulf. Silic. Relat. Elem., 2009, vol. 184, p. 1796.

    Article  CAS  Google Scholar 

  30. Kefayati, H., Vazifeh, M., and Kazemi-Rad, R., J. Chin. Chem. Soc., 2013, vol. 60, p. 1197.

    CAS  Google Scholar 

  31. Kefayati, H., Mirfarhadi, S.M., and Kazemi-Rad, R., J. Chin. Chem. Soc., 2015, vol. 62, p. 107.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hassan Kefayati.

Additional information

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kefayati, H., Khandan, S. & Tavancheh, S. One-pot three components synthesis of novel 2-iminoquinazolines and 2-imino spiro[indoline-quinazoline/pyrimidine]ones catalyzed by sodium fluoride. Russ J Gen Chem 85, 1757–1762 (2015). https://doi.org/10.1134/S1070363215070300

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215070300

Keywords

Navigation