Skip to main content
Log in

(±)-Camphor-10-sulfonic acid catalyzed atom efficient and green synthesis of triazolo[1,2-a]indazole-triones and spiro triazolo[1,2-a]indazole-tetraones

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

Abstract

(±)-Camphor-10-sulfonic acid is used for the synthesis of triazolo[1,2-a]indazole-triones and spiro triazolo[1,2-a]indazole-tetraones by condensation reaction of dimedone, urazole and aromatic aldehydes or isatin. The noteworthy aspects of this new method are high yields, high atom efficiency, use of non-toxic solvent, mild conditions, simple workup and synthesis of complex molecules using an eco-friendly, inexpensive catalyst.

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
Scheme 3
Fig. 2
Fig. 3

Similar content being viewed by others

References

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

    Book  Google Scholar 

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

    Article  CAS  Google Scholar 

  3. A. Domling, Chem. Rev. 17, 106 (2006)

    Google Scholar 

  4. E.J. Noga, G.T. Barthalmus, M.K. Mitchell, Cell Biol. Int. Rep. 10, 239–247 (1986)

    Article  CAS  Google Scholar 

  5. P.N. Craig, Comprehensive Medicinal Chemistry, vol. 8 (Pergamon, New York, 1991)

    Google Scholar 

  6. T. Kodama, M. Tamura, T. Oda, Y. Yamazaki, M. Nishikawa, S. Takemura, T. Doi, Y. Yoshinori, M. Ohkuchi, U.S. Patent 983,928, 2003

    Google Scholar 

  7. A. Kiriazis, T. Ruffer, S. Jantti, H. Lang, J. Yli-Kauhaluama, J. Comb. Chem. 9, 263–266 (2007)

    Article  CAS  Google Scholar 

  8. T.H. Kang, K. Matsumoto, Y. Murakami, H. Takayama, M. Kitajima, N. Aimi, H. Watanabe, Eur. J. Pharmacol. 444, 39–45 (2002)

    Article  CAS  Google Scholar 

  9. J. Ma, S.M. Hecht, Chem. Commun. 10, 1190–1191 (2004)

    Article  Google Scholar 

  10. M.M. Khafagy, A.H.F.A. El-Wahas, F.A. Eid, A.M. El-Agrody, Farmaco 57, 715–722 (2002)

    Article  CAS  Google Scholar 

  11. S. Tanaka, K. Seguchi, K. Itoh, A. Sera, J. Chem. Soc. Perkin Trans. 1, 2335 (1994)

    Article  Google Scholar 

  12. S. Meehan, R.D. Little, J. Org. Chem. 62, 3779 (1997)

    Article  CAS  Google Scholar 

  13. P.Y.F. Deghati, M.J. Wanner, G.J. Koomen, Tetrahedron Lett. 39, 4561 (1998)

    Article  CAS  Google Scholar 

  14. A.M. Boldi, C.R. Johnson, H.O. Eissa, Tetrahedron Lett. 40, 619 (1999)

    Article  CAS  Google Scholar 

  15. Y. Arroya, J.F. Rodriguez, M. Santos, M.A. Sanz Tejedor, I. Vaco, R.J.L. Garcia, Tetrahedron Asymmetry 15, 1059 (2004)

    Article  Google Scholar 

  16. A. Bazgir, M. Seyyedhamzeh, Z. Yasaei, P. Mirzaei, Tetrahedron Lett. 48, 8790 (2007)

    Article  CAS  Google Scholar 

  17. A. Hasaninejad, A. Zare, M. Shekouhy, Tetrahedron 67, 390–394 (2011)

    Article  CAS  Google Scholar 

  18. M.A. Chari, G. Karthikeyan, A. Pandurangan, T.S. Naidu, B. Sathyaseelan, S.M. Javaid Zaidi, A. Vinu, Tetrahedron Lett. 51, 2629 (2010)

    Article  Google Scholar 

  19. H. Hamidian, S. Fozooni, A. Hassankhani, S.Z. Mohammadi, Molecules 16, 9041–9048 (2011)

    Article  CAS  Google Scholar 

  20. A. Hassankhani, E. Mosaddeghsss, S.Y. Ebrahimipour, Arab. J. Chem. 9, 786 (2011)

    Google Scholar 

  21. Y.S. Wu, J. Cai, Z.-Y. Hu, G.H. Lin, Tetrahedron Lett. 45, 8949 (2004)

    Article  CAS  Google Scholar 

  22. H.G. Cheng, C.B. Chen, F. Tan, N.J. Chang, J.-R. Chen, W.J. Xiao, Eur. J. Org. Chem. 2010, 4976 (2010)

    Article  Google Scholar 

  23. K. Kazuhiro, S. Yuu, K.J. Hisatoshi, Heterocycles 78, 2033 (2009)

    Article  Google Scholar 

  24. K. Kazuhiro, O. Yuta, K. Hisatoshi, Synthesis 9, 1494 (2009)

    Google Scholar 

Download references

Acknowledgments

We are grateful to Department of Chemistry, Shivaji University, Kolhapur for providing spectral analysis.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dattatray R. Chandam.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chandam, D.R., Mulik, A.G., Patil, P.P. et al. (±)-Camphor-10-sulfonic acid catalyzed atom efficient and green synthesis of triazolo[1,2-a]indazole-triones and spiro triazolo[1,2-a]indazole-tetraones. Res Chem Intermed 41, 761–771 (2015). https://doi.org/10.1007/s11164-013-1226-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-013-1226-9

Keywords

Navigation