Skip to main content
SpringerLink
Log in

First synthesis of tert-butyl-substituted [1,2,4]triazino[5,6-b]indole-3-thiols and indolo[2,3-b]quinoxalines

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

Abstract

In this investigation, the first introduction of a tert-butyl group into [1,2,4]triazino[5,6-b]indole and indolo[2,3-b]quinoxaline systems, leading to a series of structurally novel 8-(t-butyl)-5H-[1,2,4]triazino[5,6-b]indole-3-thiol and 9-(t-butyl)-6H-indolo[2,3-b]quinoxaline derivatives, has been achieved by condensation of tert-butyl-substituted isatins with benzene-1,2-diamine or thiosemicarbazide. The molecular structures of these newly synthesized compounds were elucidated on the basis of elemental analysis and spectral data.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. J.L. Kgokong, P.P. Smith, G.M. Matsabisa, Bioorg. Med. Chem. 13, 2935 (2005)

    Article  CAS  Google Scholar 

  2. S.M. Shelke, S.H. Bhosale, Bioorg. Med. Chem. Lett. 20, 4661 (2010)

    Article  CAS  Google Scholar 

  3. L. Gupta, N. Sunduru, A. Verma, S. Srivastava, S. Gupta, N. Goyal, P.M.S. Chauhan, Eur. J. Med. Chem. 45, 2359 (2010)

    Article  CAS  Google Scholar 

  4. P.B. Arimondo, B. Baldeyrou, W. Laine, C. Bal, F.A. Alphonse, S. Routier, G. Coudert, J.Y. Mérour, P. Colson, C. Houssier, C. Bailly, Chem. Biol. Interact. 138, 59 (2001)

    Article  CAS  Google Scholar 

  5. R. Sharma, A.K. Pandey, R. Shivahare, K. Srivastava, S. Gupta, P.M.S. Chauhan, Bioorg. Med. Chem. Lett. 24, 298 (2014)

    Article  CAS  Google Scholar 

  6. K. Ramesh, S.N. Murthy, K. Karnakar, Y.V.D. Nageswar, Tetrahedron Lett. 52, 4734 (2011)

    Article  CAS  Google Scholar 

  7. E.S.H.E. Ashry, E.S. Ramadan, H.M.A. Hamid, M. Hagar, Synlett 723 (2004)

  8. K. Manna, Y.K. Agrawal, Bioorg. Med. Chem. Lett. 19, 2688 (2009)

    Article  CAS  Google Scholar 

  9. A.V. Ivachtchenko, A.P. Il’yin, V.V. Kobak, D.A. Zolotarev, L.V. Boksha, A.S. Trifilenkov, D.M. Ugoleva, J. Comb. Chem. 4, 419 (2002)

    Article  CAS  Google Scholar 

  10. K.R.J. Thomas, P. Tyagi, J. Org. Chem. 75, 8100 (2010)

    Article  CAS  Google Scholar 

  11. P. Tyagi, A. Venkateswararao, K.R.J. Thomas, J. Org. Chem. 76, 4571 (2011)

    Article  CAS  Google Scholar 

  12. A. Moreau, P.N.P. Rao, E.E. Knaus, Bioorg. Med. Chem. 14, 5340 (2006)

    Article  CAS  Google Scholar 

  13. N.T. Huy, K. Mizunuma, K. Kaur, N.T.T. Nhien, M. Jain, D.T. Uyen, S. Harada, R. Jain, K. Kamei, Antimicrob. Agents Chemother. 51, 2842 (2007)

    Article  CAS  Google Scholar 

  14. M. Murakata, M. Kimura, Tetrahedron Lett. 51, 4950 (2010)

    Article  CAS  Google Scholar 

  15. J. Vinsova, K. Cermakova, A. Tomeckova, M. Ceckova, J. Jampilek, P. Cermak, J. Kunes, M. Dolezal, F. Staud, Bioorg. Med. Chem. 14, 5850 (2006)

    Article  CAS  Google Scholar 

  16. M. Inagaki, S. Matsumoto, T. Tsuri, J. Org. Chem. 68, 1128 (2003)

    Article  CAS  Google Scholar 

  17. T. Duan, K. Fan, C. Zhong, T. Peng, J. Qin, X. Chen, RSC Adv. 2, 7081 (2012)

    Article  CAS  Google Scholar 

  18. Ł. Łapok, A. Siudak, M. Nowakowska, Tetrahedron Lett. 54, 3816 (2013)

    Article  Google Scholar 

  19. Y. Li, W.T. Gao, Syn. Commun. 42, 2067 (2012)

    Article  CAS  Google Scholar 

  20. Y. Li, X.Y. Tao, G.H. Lin, W.T. Gao, Heterocycl. Commun. 18, 207 (2012)

    CAS  Google Scholar 

  21. R.E. Dolle, K.H. Nelson Jr, J. Comb. Chem. 1, 235 (1999)

    Article  CAS  Google Scholar 

  22. H. Zhang, Y. Li, W.T. Gao, Helv. Chim. Acta 96, 2134 (2013)

    Article  CAS  Google Scholar 

  23. W.T. Gao, X.D. Xing, Y. Li, S. Lan, Tetrahedron 70, 2180 (2014)

    Article  CAS  Google Scholar 

  24. T. Sandmeyer, Helv. Chim. Acta 2, 234 (1919)

    Article  CAS  Google Scholar 

  25. D.D. Kenning, K.A. Mitchell, T.R. Calhoun, M.R. Funfar, D.J. Sattler, S.C. Rasmussen, J. Org. Chem. 67, 9073 (2002)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful for financial support from the Scientific Research Foundation of the Education Department of Liaoning Province (grant no. L2013428).

Author information

Authors and Affiliations

  1. Institute of Superfine Chemicals, Bohai University, Jinzhou, 121000, China

    Mingyue Lv, Hongmei Zheng, Yang Li & Wentao Gao

Authors
  1. Mingyue Lv
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hongmei Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wentao Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yang Li.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lv, M., Zheng, H., Li, Y. et al. First synthesis of tert-butyl-substituted [1,2,4]triazino[5,6-b]indole-3-thiols and indolo[2,3-b]quinoxalines. Res Chem Intermed 41, 6927–6939 (2015). https://doi.org/10.1007/s11164-014-1788-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-014-1788-1

Keywords

Search

Navigation