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Research on Chemical Intermediates

, Volume 41, Issue 7, pp 4133–4139 | Cite as

An efficient and ecocompatible synthesis of annulated benzothiazoloquinazolines in SO3H-functionalized ionic liquid

  • Kailash Sharma
  • Dinesh Kumar Sharma
  • Anand Kumar Arya
  • Mahendra Kumar
Article

Abstract

Structurally diverse annulated benzothiazoloquinazolines have been synthesized by an environmentally benign, efficient, and convenient synthesis involving three-component domino reaction of 2-aminobenzothiazoles, α-tetralone, and furan-2-carbaldehyde/p-methoxybenzaldehyde using an SO3H-functionalized halogen-free ionic liquid ([MIM(CH2)4SO3H][HSO4]) as a catalyst and a reaction medium.

Keywords

Quinazolines 2-Aminobenzothiazoles SO3H-functionalized ionic liquid Catalyst 

References

  1. 1.
    B.M. Trost, Acc. Chem. Res. 35, 695–705 (2002)CrossRefGoogle Scholar
  2. 2.
    P.A. Wender, V.A. Verma, T.J. Paxton, T.H. Pillow, Acc. Chem. Res. 41, 40–49 (2008)CrossRefGoogle Scholar
  3. 3.
    J.P. Hallet, T. Welton, Chem. Rev. 111, 3508–3576 (2011)CrossRefGoogle Scholar
  4. 4.
    J.D. Holbrey, W.M. Reichert, R.P. Swatloski, G.A. Broker, R.W. Pitner, K.R. Seddon, R.D. Rogers, Green Chem. 4, 407–413 (2002)CrossRefGoogle Scholar
  5. 5.
    D.J. Connolly, D. Cusack, T.P. Sullivan, P.J. Guiry, Tetrahedron 61, 10153–101202 (2005)CrossRefGoogle Scholar
  6. 6.
    J.P. Michael, Nat. Prod. Rep. 20, 476–493 (2003)CrossRefGoogle Scholar
  7. 7.
    C.M. Maritinei-Viturro, D. Dominguez, Tetrahedron Lett. 48, 1023–1026 (2001)CrossRefGoogle Scholar
  8. 8.
    V. Alagarsamy, S.V. Raja, K. Dhanabal, Bioorg. Med. Chem. 15, 235–241 (2007)CrossRefGoogle Scholar
  9. 9.
    V. Alagarsamy, U.S. Pathak, Bioorg. Med. Chem. 15, 3457–3462 (2007)CrossRefGoogle Scholar
  10. 10.
    V. Murugan, M. Kulkarni, R.M. Anand, E.P. Kumar, B. Suresh, V.M. Reddy, Asian J. Chem. 18, 900–906 (2006)Google Scholar
  11. 11.
    P. Selvam, K. Girija, G. Nagarajan, E. De-Clerco, Indian J. Pharm. Sci. 67, 484–487 (2005)Google Scholar
  12. 12.
    M. Robin, R. Fature, A. Perichaud, J.P. Galy, Heterocycles 53, 387–395 (2000)CrossRefGoogle Scholar
  13. 13.
    A.K. Arya, M. Kumar, Green Chem. 13, 1332 (2011)CrossRefGoogle Scholar
  14. 14.
    A.K. Arya, M. Kumar, Mol. Divers. 15, 781 (2011)CrossRefGoogle Scholar
  15. 15.
    B.S. Rathor, M. Bioorg, Med. Chem. 14, 5678–5682 (2006)CrossRefGoogle Scholar
  16. 16.
    B.S. Rathore, V. Gupta, R.R. Gupta, M. Kumar, Heteroatom. Chem. 18, 81–86 (2007)CrossRefGoogle Scholar
  17. 17.
    M. Kumar, K. Sharma, R.M. Samarth, A. Kumar, Eur. J. Med. Chem. 45, 4467–4472 (2010)CrossRefGoogle Scholar
  18. 18.
    M. Kumar, K. Sharma, A.K. Arya, Tetrahedron Lett. 56, 4604 (2012)CrossRefGoogle Scholar
  19. 19.
    A.K. Arya, S. Gupta, M. Kumar, Tetrahedron Lett. 53, 6035 (2012)CrossRefGoogle Scholar
  20. 20.
    M. Kumar, K. Sharma, D.K. Sharma, A.K. Arya, Tetrahedron Lett. 54, 878–882 (2013)CrossRefGoogle Scholar
  21. 21.
    M. Kumar, K. Sharma, A.K. Fogla, K. Sharma, M. Rathore, Res. Chem. Intermed. 39, 2555–2564 (2013)CrossRefGoogle Scholar
  22. 22.
    Z. Du, Z. Li, Y. Deng, Synth. Commun. 35, 1343 (2005)CrossRefGoogle Scholar
  23. 23.
    D. Fang, Z.H. Fei, Z.L. Liu, Catal. Commun. 10, 1267 (2009)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2014

Authors and Affiliations

  • Kailash Sharma
    • 1
  • Dinesh Kumar Sharma
    • 1
  • Anand Kumar Arya
    • 2
  • Mahendra Kumar
    • 1
  1. 1.Department of ChemistryUniversity of RajasthanJaipurIndia
  2. 2.DESMRegional Institute of Education (NCERT)AjmerIndia

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