Skip to main content
SpringerLink
Log in

Efficient, microwave-mediated synthesis of benzothiazole- and benzimidazole-based heterocycles

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

Abstract

1-(Benzothiazol-2-yl)-3-(N,N-dimethylamino)-2-(phenylsulfonyl)prop-2-en-1-one (3) and 1-(1-methylbenzimidazol-2-yl)-3-(N,N-dimethylamino)-2-(phenylsulfonyl)prop-2-en-1-one (4) were obtained from the reaction of 1-(benzothiazothiazol-2-yl)-2-phenylsulfonyl-1-ethanone (1) and 1-(1-methyl-1H-benzimidazol-2-yl)-2-(phenylsulfonyl)-1-ethanone (2) with N,N-dimethylformamide dimethyl acetal, respectively. The enaminosulfones 3 and 4 were used as versatile building blocks for the synthesis of novel pyrazolo[1,5-a]pyrimidine and [1,2,4]-triazolo[1,5-a]pyramidine derivatives via their reactions with the appropriate aminopyrazoles and aminotriazole under both microwave and thermal reaction conditions. They have been also utilized as reactive synthons for the construction of novel pyrimido[1,2-a]benzimidazole, pyrido[1,2-a]benzimidazole, pyrimidine, isoxazole and pyrazole heterocycles pendent to benzothiazole and benzimidazole ring systems.

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
Scheme 4
Scheme 5
Scheme 6

Similar content being viewed by others

References

  1. D. Lednicer, Strategies for Organic Drug Synthesis and Design (Wiley, New York, 2009)

    Google Scholar 

  2. A. Váradi, T.C. Palmer, P.R. Notis, G.N. Redel-Traub, D. Afonin, J.J. Subrath, G.W. Pasternak, C. Hu, I. Sharma, S. Majumdar, Org. Lett. 16, 1668 (2014)

    Article  Google Scholar 

  3. D. Dai, J.R. Burgeson, D.N. Gharaibeh, A.L. Moore, R.A. Larson, N.R. Cerruti, S.M. Amberg, T.C. Bolken, D.E. Hruby, Bioorg. Med. Chem. Lett. 23, 744 (2013)

    Article  CAS  Google Scholar 

  4. J.R. Burgeson, A.L. Moore, D.N. Gharaibeh, R.A. Larson, N.R. Cerruti, S.M. Amberg, D.E. Hruby, D. Dai, Bioorg. Med. Chem. Lett. 23, 750 (2013)

    Article  CAS  Google Scholar 

  5. M.S. Abu-Bakr, F.A. Bassyouni, M. Abdel Rehim, Res. Chem. Intermed. 38, 2523 (2012)

    Article  CAS  Google Scholar 

  6. B. Nandha, H. Kuntal, J.N.N.S. Chandra, L.V.G. Nargund, P. Rashmi, M.S. Harish, D.S. Puranik, Der Pharm. Chem. 5, 287 (2013)

    CAS  Google Scholar 

  7. Y.L.N. Murthy, G. Durga, A. Jha, Med. Chem. Res. 22, 2266 (2013)

    Article  CAS  Google Scholar 

  8. G. Singh, M. Kaur, M. Chander, Int. Res. J. Pharm. 4, 82 (2013)

    Article  Google Scholar 

  9. V. Vajpayee, S. Lee, J.W. Park, A. Dubey, H. Kim, T.R. Cook, P.J. Stang, K.-W. Chi, Organometallics 32, 1563 (2013)

    Article  CAS  Google Scholar 

  10. A. Husain, M. Rashid, M. Shaharyar, A.A. Siddiqui, R. Mishra, Eur. J. Med. Chem. 62, 785 (2013)

    Article  CAS  Google Scholar 

  11. V.N. Telvekar, V.K. Bairwa, K. Satardekar, A. Bellubi, Bioorg. Med. Chem. Lett. 22, 649 (2012)

    Article  CAS  Google Scholar 

  12. P. Lue, J.V. Greenhill, Adv. Heterocycl. Chem. 67, 207 (1997)

  13. U. Kucklnder, in Enaminones as Synthons in the Chemistry of Enaminones, ed. by Z. Rappoport (Wiley, New York, 1944), p. 523

    Google Scholar 

  14. M.R. Shaaban, T.M.A. Eldebss, A.F. Darweesh, A.M. Farag, J. Heterocycl. Chem. 45, 1739 (2008)

    Article  CAS  Google Scholar 

  15. M.R. Shaaban, T.M.A. Eldebss, A.F. Darweesh, A.M. Farag, J. Chem. Res. 34, 8 (2010)

  16. K.R. Scott, G.O. Rankin, J.P. Stables, M.S. Alexander, I.O. Edafiogho, V.A. Farrar, K.R. Kolen,  J.A. Moore, L.D. Sims, A.D. Tonnu, J. Med. Chem. 38, 4033 (1995)

    Article  CAS  Google Scholar 

  17. J. Leibscher, M. Ptzel, Syn. Lett. 471 (1994)

  18. K. Ramaiah, P.K. Dubey, J. Ramanadham, J.S. Grossert, D.L. Hooper, Ind. J. Chem. 38, 297 (1999)

    Google Scholar 

  19. B.M. Trost, D.P. Curran, Tetrahedron Lett. 22, 1287 (1981)

    Article  CAS  Google Scholar 

  20. H.D. Becker, G.A. Russel, J. Org. Chem. 28, 1896 (1963)

    Google Scholar 

  21. P.D. Magnus, Tetrahedron 33, 2019 (1977)

    Article  CAS  Google Scholar 

  22. J.-L. Macro, I. Femandes, N. Khira, P. Fernandez, A. Romero, J. Org. Chem. 60, 667 (1995)

    Google Scholar 

  23. N. Elander, J.R. Jones, S.Y. Lu, S. Stone-Elander, Chem. Soc. Rev. 29, 239 (2000)

    Article  CAS  Google Scholar 

  24. P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 57, 9225 (2001)

    Article  Google Scholar 

  25. M. Larhed, A. Hallberg, Drug Discov. Today 6, 406 (2001)

    Article  CAS  Google Scholar 

  26. K.A. Ali, E.A. Ragab, H.S. Abdelghafar, A.M. Farag, Res. Chem. Intermed. (2015). doi:10.1007/s11164-015-2231-y

    Google Scholar 

  27. A.F. Darweesh, A.E.M. Mekky, A.A. Salman, A.M. Farag, Heterocycles 89, 113 (2014)

    Article  CAS  Google Scholar 

  28. A.E.M. Mekky, A.F. Darweesh, A.A. Salman, A.M. Farag, Heterocycles 89, 1827 (2014)

    Article  CAS  Google Scholar 

  29. B. Hegazi, H. Abdel-Gawad, H.A. Mohamed, F.A. Badria, A.M. Farag, J. Heterocycl. Chem. 50, 355 (2013)

    Article  CAS  Google Scholar 

  30. K.A. Ali, M.A. Elsayed, A.M. Farag, Heterocycles 85, 1913 (2012)

    Article  CAS  Google Scholar 

  31. M.R. Shaaban, T.S. Saleh, A.S. Mayhoub, A.M. Farag, Eur. J. Med. Chem. 46, 3690 (2011)

    Article  CAS  Google Scholar 

  32. A.M. Farag, K.A.K. Ali, T. El-Debss, A.S. Mayhoub, A.E. Amr, N.A. Abdel-Hafez, M.M. Abdulla, Eur. J. Med. Chem. 45, 5887 (2010)

    Article  CAS  Google Scholar 

  33. Y.N. Mabkhot, N.A. Kheder, A.M. Farag, Heterocycles 81, 2369 (2010)

    Article  CAS  Google Scholar 

  34. A.M. Farag, N.A. Kheder, Y.N. Mabkhot, Heterocycles 78, 1787 (2009)

    Article  CAS  Google Scholar 

  35. A.M. Farag, A.S. Mayhoub, S.E. Barakat, A.H. Bayomi, Bioorg. Med. Chem. 16, 881 (2008)

    Article  CAS  Google Scholar 

  36. A.M. Farag, A.S. Mayhoub, S.E. Barakat, A.H. Bayomi, Bioorg. Med. Chem. 16, 4569 (2008)

    Article  CAS  Google Scholar 

  37. M.R. Shaaban, T.S. Saleh, A.S. Mayhoub, A. Mansour, A.M. Farag, Bioorg. Med. Chem. 16, 6344 (2008)

    Article  CAS  Google Scholar 

  38. M.H. Elnagdi, F.A. Abdel All, R.M. Abdel Motaleb, F.F. Mahmoud, Collect. Czech. Chem. Commun. 54, 1082 (1989)

    Article  CAS  Google Scholar 

  39. S.M. Sherief, A.M. Hussien, Monatsh. Chem. 128, 687 (1997)

    Article  Google Scholar 

  40. A. Takamizawa, Y. Hamashima, Yakugaku Zasshi 84, 1113 (1964)

    CAS  Google Scholar 

  41. M.H. Elnagdi, E.M. Kandeel, E.M. Zayed, Z.E. Kandeel, J. Heterocycl. Chem. 14, 155 (1977)

    Article  CAS  Google Scholar 

  42. K.C. Joshi, V.N. Pathak, U. Garg, J. Heterocycl. Chem. 16, 1141 (1979)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

A. F. Darweesh is very thankful to Prof. Peter Metz [Technische Universität (TU)-Dresden] for giving him the chance to carry out spectral analysis at his laboratory during the Alexander von Humboldt fellowships: July 2012–July 2014. He also is deeply thankful to the Alexander von Humboldt Foundation (AvH) for granting him fellowships from July 2012–July 2014 at TU-Dresden. Amani A. Salman is very thankful to Prof. Kamal M. Dawood (Cairo University) for giving her the facilities for carrying out microwave experiments.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt

    Ahmed F. Darweesh, Ahmed E. M. Mekky, Amani A. Salman & Ahmad M. Farag

  2. Chemistry Department, Faculty of Science, King Abdulaziz University, North Jeddah, P.O. Box 80203, Jeddah, 21589, Saudi Arabia

    Ahmed E. M. Mekky

Authors
  1. Ahmed F. Darweesh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ahmed E. M. Mekky
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Amani A. Salman
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ahmad M. Farag
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ahmad M. Farag.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Darweesh, A.F., Mekky, A.E.M., Salman, A.A. et al. Efficient, microwave-mediated synthesis of benzothiazole- and benzimidazole-based heterocycles. Res Chem Intermed 42, 4341–4358 (2016). https://doi.org/10.1007/s11164-015-2279-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2279-8

Keywords

Search

Navigation