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An economic, simple and convenient synthesis of 2-aryl/heteroaryl/styryl/alkylbenzothiazoles using SiO2–HNO3

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Abstract

The present work was undertaken to develop an economic method for the synthesis of 2-aryl/heteroaryl/styryl/alkylbenzothiazoles mediated by SiO2–HNO3. In this report, we have demonstrated the catalytic potential of SiO2–HNO3 for the oxidative condensation of 2-aminothiophenol and aldehydes. Instant reaction at room temperature under solvent-free condition, high substrate to catalyst ratio 50:1 (by weight), practical application by large-scale synthesis, and excellent yields are the main advantages of the present protocol.

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References

  1. I. Hutchinson, T.D. Bradshaw, M.F.G. Matthews Stevens, A.D. Westwell, Bioorg. Med. Chem. Lett. 13, 471 (2003)

    Article  CAS  Google Scholar 

  2. S.J. Ji, H.B. Shi, Dyes Pigment 70, 246 (2006)

    Article  CAS  Google Scholar 

  3. R.G. Caccese, J.F. Di Joseph, J.S. Scotnicki, L.E. Borella, L.M. Adams, Agents Act. 34, 223 (1991)

    Article  CAS  Google Scholar 

  4. L. Racane, M. Kralj, L. Suman, R. Stojkovic, V.T. Kulenovic, G.K. Zamola, Bioorg. Med. Chem. 18, 1038 (2010)

    Article  CAS  Google Scholar 

  5. P.J. Palmer, R.B. Trigg, J.V. Warrington, J. Med. Chem. 14, 248 (1971)

    Article  CAS  Google Scholar 

  6. P. Hrobarik, P. Zahradnik, W.M.F. Fabian, Phys. Chem. Chem. Phys. 6, 495 (2004)

    Article  CAS  Google Scholar 

  7. M. Zajac, P. Hrobarik, P. Magdolen, P. Foltinova, P. Zahradnik, Tetrahedron 64, 10605 (2008)

    Article  CAS  Google Scholar 

  8. P. Hrobarik, I. Sigmundova, P. Zahradnik, P. Kasak, V. Arion, E. Franz, K. Clays, J. Phys. Chem. C 114, 22289 (2010)

    Article  CAS  Google Scholar 

  9. P. Hrobarik, V. Harobarikova, I. Sigmundova, P. Zahradnik, M. Fakis, I. Polyzos, P. Persephonis, J. Org. Chem. 76, 8726 (2011)

    Article  CAS  Google Scholar 

  10. T. Itoh, K. Nagata, H. Ishikawa, A. Ohsawa, Heterocycles 63, 2769 (2004). (Sc(OTF)3)

    Article  CAS  Google Scholar 

  11. K. Bougrin, A. Loupy, M. Soufiaoui, Tetrahedron 54, 8055 (1998). (MnO2/SiO2)

    Article  CAS  Google Scholar 

  12. S. Rostamizadeh, K.S.A. Housaini, Phosphorus Sulfur Silicon Elem 180, 1321 (2005). (p-TsOH/graphite)

    Article  CAS  Google Scholar 

  13. Y. Li, G.Y. Wang, J.Y. Wang, L. Jacquline, Chem. Lett. 35, 460 (2006). (I2/DMF)

    Article  CAS  Google Scholar 

  14. F. Al-Qalaf, R.R. Mekheimer, K.U. Sadek, Molecules 13, 2908 (2008). (CAN)

    Article  CAS  Google Scholar 

  15. P.S. Chandrachood, D.R. Garud, T.V. Gadakari, R.C. Torane, N.R. Deshpande, R.V. Kashalkar, Acta Chim. Slov. 58, 367 (2011). (Co(NO3)2)

    CAS  Google Scholar 

  16. N. Azizi, A.K. Amiri, R. Baghi, M. Bolourtchian, M.M. Hashemi, Monatsh. Chem. 140, 1471 (2009). (p-TsOH)

    Article  CAS  Google Scholar 

  17. A.K. Chakraborti, S. Rudrawar, K.B. Jadhav, G. Kaur, S.V. Chankeshwara, Green Chem. 9, 1335 (2007). (H2O/reflux)

    Article  CAS  Google Scholar 

  18. N. Parikh, D. Kumar, S.R. Roy, A.K. Chakraborti, J. Chem. Soc. Chem. Commun. 47, 1797 (2011). (SODSS)

    Article  CAS  Google Scholar 

  19. M. Kodomari, Y. Tamaru, T. Aoyama, Synth. Commun. 34, 3029 (2004). (SiO2/MW)

    Article  CAS  Google Scholar 

  20. H. Sharghi, O. Asemani, Synth. Commun. 39, 860 (2009). (MeSO3H/SiO2)

    Article  CAS  Google Scholar 

  21. H. Mutsushita, S.H. Lee, M. Joung, B. Clapham, K.D. Janda, Tetrahedron Lett. 45, 313 (2004). (AlMe3)

    Article  Google Scholar 

  22. D.L. Boger, J. Org. Chem. 43, 2296 (1978). (P2O5/MeSO3H)

    Article  CAS  Google Scholar 

  23. A.K. Chakraborti, S. Rurdawar, G. Kaur, L. Sharma, Synletter 9, 1533 (2004). (NMP)

    Article  Google Scholar 

  24. A.K. Chakraborti, C. Selvam, G. Kaur, S. Bhagat, Synletter 5, 851 (2004). (MW)

    Article  Google Scholar 

  25. S. Rurdawar, A. Kondaskar, A.K. Chakraborti, Synthesis 15, 2521 (2005). (SOCl2)

    Google Scholar 

  26. C. Siddappa, V. Kambappa, M. Umashankara, K.S. Rangappa, Tetrahedron Lett. 52, 5474 (2011). (I2/t-BuOK)

    Article  CAS  Google Scholar 

  27. D. Alagille, R.M. Baldwin, G.D. Tamagnan, Tetrahedron Lett. 46, 1349 (2005). (Pd(OAc)2, Cs2CO3)

    Article  CAS  Google Scholar 

  28. R.H. Tale, Org. Lett. 4, 1641 (2002). (CAN)

    Article  CAS  Google Scholar 

  29. C. Zhu, T. Akiyama, Synletter 16, 2457 (2010). (DMSO)

    Google Scholar 

  30. X.J. Mu, J.P. Zou, R.S. Zeng, J.C. Wu, Tetrahedron Lett. 46, 4345 (2005). (Mn(OAc)3)

    Article  CAS  Google Scholar 

  31. S.D. Bose, M. Idrees, B. Srikant, Synthesis 6, 819 (2007). (DDQ)

    Article  Google Scholar 

  32. G. Evindar, R.A. Batey, J. Org. Chem. 71, 1802 (2006). (CuI/1,10-Phen)

    Article  CAS  Google Scholar 

  33. V.Z. Shirinian, S.Y. Melkova, L.I. Belenkii, M.M. Krayushkin, Russ. Chem. Bull. Int. Ed. 49, 1859 (2000)

    Article  CAS  Google Scholar 

  34. G.M. Raghavendra, A.B. Ramesha, C.N. Revanna, K.N. Nandeesh, K. Mantelingu, K.S. Rangappa, Tetrahedron Lett. 52, 5571 (2011). (T3P/DMSO)

    Article  CAS  Google Scholar 

  35. K. Bahrami, M.M. Khodaei, F. Naali, J. Org. Chem. 73, 6835 (2008). (H2O2/CAN)

    Article  CAS  Google Scholar 

  36. S.D. Gupta, H.P. Singh, N.S.H.N. Moorthy, Synth. Commun. 37, 4327 (2007). (I2)

    Article  CAS  Google Scholar 

  37. K.S. Niralwad, B.B. Shingate, M.S. Shingare, Bull. Korean Chem. Soc. 31, 981 (2010). (SiO2-H2SO4)

    Article  CAS  Google Scholar 

  38. G.F. Chen, L.Y. Zhang, H.M. Jia, B.H. Chen, J.T. Li, S.X. Wang, G. Wi, Res. Chem. Intermed. 39, 2077 (2013)

    Article  CAS  Google Scholar 

  39. I. Mohammadpoor-Baltork, M.A. Zolfigol, M. Abdollahi-Alibeik, Tetrahedron Lett. 45, 8687 (2004)

    Article  CAS  Google Scholar 

  40. D. Azarifar, M.A. Zolfigol, B. Maleki, Synthesis 11, 1744 (2004)

    Article  Google Scholar 

  41. M.A. Zolfigol, K. Amani, M. Hajjami, A. Ghorbani-Choghamarani, R. Ayazi-Nasrabadi, S. Jafari, Catal. Commun. 9, 1739 (2008)

    Article  CAS  Google Scholar 

  42. A. Ghorbani-Choghamarani, M. Nikoorazm, H. Goudarziafshar, L. Shiri, Z. Chenani, Bull. Korean Chem. Soc. 30, 972 (2009)

    Article  CAS  Google Scholar 

  43. P. Kumar, A. Kumar, K. Hussain, Ultrasonics Sonochem. 19, 729 (2012)

    Article  CAS  Google Scholar 

  44. M. Abdollahi-Alibeik, S. Poorirani, Phosphorus Sulfur Silicon Relat. Elem. 184, 3182 (2009). (HClO4)

    Article  CAS  Google Scholar 

  45. X.-L. Yang, C.-M. Xu, S.-M. Lin, J.-X. Chen, J.-C. Ding, H.-Y. Wu, W.-K. Su, J. Braz. Chem. Soc. 21(1), 37 (2010). (CTAB/H2O)

    Article  CAS  Google Scholar 

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Acknowledgment

Financial support as a junior research fellowship by the Haryana State Council of Science and Technology is gratefully acknowledged for accomplishing this work.

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Authors and Affiliations

  1. Department of Chemistry, Kurukshetra University, Kurukshetra, 136119, Haryana, India

    Parvin Kumar, Rimpy Bhatia, Dinesh Kumar, Ramesh C. Kamboj, Suresh Kumar, Raj Kamal & Ramesh Kumar

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  1. Parvin Kumar
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  2. Rimpy Bhatia
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  3. Dinesh Kumar
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Correspondence to Parvin Kumar or Ramesh C. Kamboj.

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Kumar, P., Bhatia, R., Kumar, D. et al. An economic, simple and convenient synthesis of 2-aryl/heteroaryl/styryl/alkylbenzothiazoles using SiO2–HNO3 . Res Chem Intermed 41, 4283–4292 (2015). https://doi.org/10.1007/s11164-013-1529-x

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