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Vitamin C as a green and robust catalyst for the fast and efficient synthesis of valuable organic compounds via multi-component reactions in water

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Abstract

In the present paper, we report l-ascorbic acid (vitamin C) as an efficient and robust catalyst for the straightforward synthesis of various organic compounds, including carboxamide, benzodiazepine and benzoxazepine derivatives. These compounds with potential drug value which exhibit a broad spectrum biological and pharmacological activities were successfully accessed with vitamin C catalytic system under environmentally friendly conditions in water. The main advantages of this protocol are operational simplicity, mild reaction conditions, high yields in short reaction time and good substrate generality.

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References

  1. J.H. Clark, Green Chem. 1, 1 (1999)

    Article  CAS  Google Scholar 

  2. D.T. Allen, K.S. Rosselot, Pollution prevention for chemical processes (Wiley-Interscience, Hoboken, 1997)

    Google Scholar 

  3. M.B. Gawande, V.D. Bonifácio, R. Luque, P.S. Branco, R.S. Varma, Chem Soc Rev 42, 5522 (2013)

    Article  CAS  PubMed  Google Scholar 

  4. N. Marion, S. Díez-González, S.P. Nolan, Angew Chem Int Ed 46, 2988 (2007)

    Article  CAS  Google Scholar 

  5. D. Yao, G. Li, T. Kuila, P. Li, N.H. Kim, S.I. Kim, J.H. Lee, J. Appl. Polym. Sci. 120, 1114 (2011)

    Article  CAS  Google Scholar 

  6. H.-P. Zhu, F. Yang, J. Tang, M.-Y. He, Green Chem. 5, 38 (2003)

    Article  CAS  Google Scholar 

  7. S. Noura, M. Ghorbani, M.A. Zolfigol, M. Narimani, M. Yarie, M. Oftadeh, J. Mol. Liq. 271, 778 (2018)

    Article  CAS  Google Scholar 

  8. T.-K. Huang, R. Wang, L. Shi, X.-X. Lu, Catal. Commun. 9, 1143 (2008)

    Article  CAS  Google Scholar 

  9. W. Yang, D.-M. Du, Org. Lett. 12, 5450 (2010)

    Article  CAS  PubMed  Google Scholar 

  10. J.P. Malerich, K. Hagihara, V.H. Rawal, J. Am. Chem. Soc. 130, 14416 (2008)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Ł. Albrecht, G. Dickmeiss, F.C. Acosta, C. Rodríguez-Escrich, R.L. Davis, K.A. Jørgensen, J. Am. Chem. Soc. 134, 2543 (2012)

    Article  CAS  PubMed  Google Scholar 

  12. S. Schenker, A. Zamfir, M. Freund, S.B. Tsogoeva, Eur. J. Org. Chem. 2011, 2209 (2011)

    Article  CAS  Google Scholar 

  13. Y. Takemoto, Org. Biomol. Chem. 3, 4299 (2005)

    Article  CAS  PubMed  Google Scholar 

  14. J. Wang, H. Li, X. Yu, L. Zu, W. Wang, Org. Lett. 7, 4293 (2005)

    Article  CAS  PubMed  Google Scholar 

  15. B. Frei, S. Lawson, Proc. Natl. Acad. Sci. 105, 11037 (2008)

    Article  PubMed  Google Scholar 

  16. M.L. Heaney, J.R. Gardner, N. Karasavvas, D.W. Golde, D.A. Scheinberg, E.A. Smith, O.A. O’Connor, Cancer Res 68, 8031 (2008)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. H.H. Ting, F.K. Timimi, K.S. Boles, S.J. Creager, P. Ganz, M.A. Creager, J. Clin. Investig. 97, 22 (1996)

    Article  CAS  PubMed  Google Scholar 

  18. G.R. Buettner, B.A. Jurkiewicz, Radiat. Res. 145, 532 (1996)

    Article  CAS  PubMed  Google Scholar 

  19. M. Shiri, Chem. Rev. 112, 3508 (2012)

    Article  CAS  PubMed  Google Scholar 

  20. C. Dittrich, V. Dieras, P. Kerbrat, C. Punt, R. Sorio, F. Caponigro, X. Paoletti, C. de Balincourt, D. Lacombe, P. Fumoleau, Investig New Drugs 21, 347 (2003)

    Article  CAS  Google Scholar 

  21. N. Willand, T. Beghyn, G. Nowogrocki, J.-C. Gesquiere, B. Deprez, Tetrahedron Lett 45, 1051 (2004)

    Article  CAS  Google Scholar 

  22. S. Arayachukiat, C. Kongtes, A. Barthel, S.V. Vummaleti, A. Poater, S. Wannakao, L. Cavallo, V. D’Elia, A.C.S. Sustain, Chem. Eng. 5, 6392 (2017)

    CAS  Google Scholar 

  23. A.A. Napoleon, F.-R.N. Khan, E.D. Jeong, E.H. Chung, Tetrahedron Lett 55, 5656 (2014)

    Article  CAS  Google Scholar 

  24. M. Mahyari, M.S. Laeini, A. Shaabani, Chem. Commun. 50, 7855 (2014)

    Article  CAS  Google Scholar 

  25. R. Mohammadian, M.K. Alavijeh, N. Kamyar, M.M. Amini, A. Shaabani, Polyhedron 156, 174 (2018)

    Article  CAS  Google Scholar 

  26. A. Shaabani, R. Mohammadian, H. Farhid, M.K. Alavijeh, M.M. Amini, Ind. Eng. Chem. Res. 58, 2784 (2019)

    Article  CAS  Google Scholar 

  27. A. Shaabani, R. Mohammadian, A. Hashemzadeh, R. Afshari, M.M. Amini, New J. Chem. 42, 4167 (2018)

    Article  CAS  Google Scholar 

  28. A. Shaabani, R. Mohammadian, S.E. Hooshmand, A. Hashemzadeh, M.M. Amini, ChemistrySelect 2, 11906 (2017)

    Article  CAS  Google Scholar 

  29. A. Shaabani, A. Rashidi Vahid, S. Shaabani, R. Mohammadian, M.T. Nazeri, M. Keramati Nejad, Appl. Organomet. Chem. e4510 (2018)

  30. A. Shaabani, A. Maleki, J. Moghimi-Rad, J. Org. Chem. 72, 6309 (2007)

    Article  CAS  PubMed  Google Scholar 

  31. A. Shaabani, H. Mofakham, A. Maleki, F. Hajishaabanha, J. Combin. Chem. 12, 630 (2010)

    Article  CAS  Google Scholar 

  32. A. Shaabani, E. Soleimani, A.H. Rezayan, A. Sarvary, H.R. Khavasi, Org. Lett. 10, 2581 (2008)

    Article  CAS  PubMed  Google Scholar 

  33. S. Shaabani, A. Shaabani, S.W. Ng, ACS Combin. Sci. 16, 176 (2014)

    Article  CAS  Google Scholar 

  34. A. Shaabani, S.E. Hooshmand, M.T. Nazeri, R. Afshari, S. Ghasemi, Tetrahedron Lett. 57, 3727 (2016)

    Article  CAS  Google Scholar 

  35. L.A. Polindara-García, E. Juaristi, Eur. J. Org. Chem. 2016, 1095 (2016)

    Article  CAS  Google Scholar 

  36. T. Bousquet, M. Jida, M. Soueidan, R. Deprez-Poulain, F. Agbossou-Niedercorn, L. Pelinski, Tetrahedron Lett. 53, 306 (2012)

    Article  CAS  Google Scholar 

  37. M. Adib, E. Sheikhi, M. Azimzadeh, Tetrahedron Lett. 56, 1933 (2015)

    Article  CAS  Google Scholar 

  38. R. Ramozzi, K. Morokuma, J. Org. Chem. 80, 5652 (2015)

    Article  CAS  PubMed  Google Scholar 

  39. A. Shaabani, M.B. Teimouri, J. Chem. Res. 2002, 433 (2002)

    Article  Google Scholar 

  40. J.N. Sangshetti, A.S. Zambare, F.A. Kalam Khan, I. Gonjari, Z. Zahir, Mini Rev. Med. Chem. 14, 988 (2014)

    Article  CAS  PubMed  Google Scholar 

  41. G.A. Archer, L.H. Sternbach, Chem. Rev. 68, 747 (1968)

    Article  CAS  Google Scholar 

  42. A. Shaabani, A. Maleki, H. Mofakham, J. Combin. Chem. 10, 595 (2008)

    Article  CAS  Google Scholar 

  43. M. Ghandi, T. Momeni, M.T. Nazeri, N. Zarezadeh, M. Kubicki, Tetrahedron Lett. 54, 2983 (2013)

    Article  CAS  Google Scholar 

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Acknowledgements

We gratefully acknowledge financial support of the Research Council of Shahid Beheshti University and the Iran National Science Foundation (INSF).

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Authors and Affiliations

  1. Faculty of Chemistry, Shahid Beheshti University, G.C., P.O. Box 19396-4716, Tehran, Iran

    Ahmad Shaabani, Vida Khodkari, Mohammad Taghi Nazeri, Shima Ghasemi, Reza Mohammadian & Shabnam Shaabani

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  1. Ahmad Shaabani
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  2. Vida Khodkari
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  3. Mohammad Taghi Nazeri
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  4. Shima Ghasemi
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  5. Reza Mohammadian
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Correspondence to Ahmad Shaabani.

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Shaabani, A., Khodkari, V., Nazeri, M.T. et al. Vitamin C as a green and robust catalyst for the fast and efficient synthesis of valuable organic compounds via multi-component reactions in water. J IRAN CHEM SOC 16, 1793–1800 (2019). https://doi.org/10.1007/s13738-019-01655-w

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  • DOI: https://doi.org/10.1007/s13738-019-01655-w

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