Skip to main content

Advertisement

Log in

Benzo[h]thiazolo[2,3-b]quinazolines by an efficient p-toluenesulfonic acid-catalyzed one-pot two-step tandem reaction

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A highly efficient method has been developed for synthesis of 7,9-disubstituted-6,7-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazolines via multicomponent one-pot two-step tandem reaction involving 1-tetralone, arylaldehydes, thiourea, and 4-chlorophenacyl bromide/(3-bromoacetyl)coumarin utilizing p-toluenesulfonic acid as catalyst in glacial acetic acid under reflux conditions. Analytically pure products are formed with excellent yield and short reaction time. All the synthesized compounds were confirmed by their spectral and elemental analyses.

Graphical abstract

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.

Fig. 1
Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. S.A. Abdel-Mohsen, J. Chin. Chem. Soc. 50, 1085 (2003)

    Article  CAS  Google Scholar 

  2. A.C. Robert, A.G. Richard, F.C. Zdzislaw, J. Med. Chem. 17, 1025 (1974)

    Article  Google Scholar 

  3. S.F. Mohamed, E.M. Flefel, A.E. Amr, D.N. Abd El-Shafy, Eur. J. Med. Chem. 45, 1494 (2010)

    Article  CAS  Google Scholar 

  4. S. Maddila, G.L.V. Damu, E.O. Oseghe, O.A. Abafe, C. Venakata Rao, P. Lavanya, J. Korean Chem. Soc. 56, 334 (2012)

    Article  CAS  Google Scholar 

  5. E.E. Flefel, M.A. Salama, M. El-Shahat, M.A. El-Hashash, A.F. El-Farargy, Phosphorus Sulfur Silicon Relat. Elem. 182, 1739 (2007)

    Article  CAS  Google Scholar 

  6. B. Tozkoparan, M. Ertan, P. Kelicen, R. Demirdamar, Farmaco 54, 588 (1999)

    Article  CAS  Google Scholar 

  7. E. Jeanneau-Nicolle, M. Benoit-Guyod, A. Namil, G. Leclerc, Eur. J. Med. Chem. 27, 115 (1992)

    Article  CAS  Google Scholar 

  8. E.A. Abd El-Galil, S.S. Maigali, M.M. Abdulla, Monatsh. Chem. 139, 1409 (2008)

    Article  Google Scholar 

  9. K. Danel, E.B. Pedersen, C. Nielsen, J. Med. Chem. 41, 191 (1998)

    Article  CAS  Google Scholar 

  10. B. Pan, R. Huang, L. Zheng, C. Chen, S. Han, D. Qu, M. Zhu, P. Wei, Eur. J. Med. Chem. 46, 819 (2011)

    Article  CAS  Google Scholar 

  11. A. Balkan, S. Uma, M. Ertan, W. Wiegrebe, Pharmazie 47, 687 (1992)

    CAS  Google Scholar 

  12. J. Wichmann, G. Adam, S. Kolczewski, V. Mutel, T. Woltering, Bioorg. Med. Chem. Lett. 9, 1573 (1999)

    Article  CAS  Google Scholar 

  13. S. Ruiu, G. Marchese, P.L. Saba, G.L. Gessa, L. Pani, Mol. Psychiatr. 5, 673 (2000)

    Article  CAS  Google Scholar 

  14. M.A. Fadi, Sci. Pharm. 76, 415 (2008)

    Article  Google Scholar 

  15. C.N. Khobragade, R.G. Bodade, B.S. Dawane, S.G. Konda, N.T. Khandare, J. Enzyme Inhib. Med. Chem. 25, 615 (2010)

    Article  CAS  Google Scholar 

  16. H. Zhi, L.M. Chen, L.L. Zhang, S.J. Liu, D.C.C. Wan, H.Q. Lin, C. Hu, Arkivoc xiii, 266 (2008)

    Google Scholar 

  17. S. Kolb, O. Mondesert, M.-L. Goddard, D. Jullien, B.O. Villoutreix, B. Ducommun, C. Garbay, E. Braud, Chem. Med. Chem. 4, 633 (2009)

    Article  CAS  Google Scholar 

  18. M.M. Ghorab, S.M. Abdel-Gawad, M.S. El-Gaby, Farmaco 55, 249 (2000)

    Article  CAS  Google Scholar 

  19. B. Janardhan, K. Manjulatha, B. Srinivas, B. Rajitha, N. Muralikrishna, A. Sadanandam, RSC Adv. 4, 22866 (2014)

    Article  Google Scholar 

  20. A.A. Abu-Hashem, M.M. Youssef, H.A.R. Hussein, J. Chin. Chem. Soc. 58, 41 (2011)

    Article  CAS  Google Scholar 

  21. B. Janardhan, B. Srinivas, B. Rajitha, A.C. Peter, Tetrahedron Lett. 55, 224 (2014)

    Article  CAS  Google Scholar 

  22. J. Zhu, H. Bienayme, Multicomponent Reactions (Wiley-VCH, Weinheim, 2005)

    Book  Google Scholar 

  23. A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)

    Article  CAS  Google Scholar 

  24. A. Gursoy, N. Karali, Turk. J. Chem. 27, 545 (2003)

    Google Scholar 

Download references

Acknowledgments

The authors would like to thank the Head, Department of Chemistry, Osmania University for providing research facilities. B. Sonyanaik thanks the University Grant Commission (UGC), New Delhi for financial assistance.

Conflict of interest

The authors report no conflicts of interest. The authors alone hereby stand responsible for the contents of this scientific paper.

Ethical standard

This article does not contain any studies with human participants or animals performed by any of the authors.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to B. Sakram.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2753 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sakram, B., Sonyanaik, B., Ashok, K. et al. Benzo[h]thiazolo[2,3-b]quinazolines by an efficient p-toluenesulfonic acid-catalyzed one-pot two-step tandem reaction. Res Chem Intermed 42, 1699–1705 (2016). https://doi.org/10.1007/s11164-015-2112-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2112-4

Keywords

Navigation