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Regioselective and solvent-free arylation of β-nitrostyrenes with mono- and dialkyl anilines

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Abstract

A green and solvent-free method were developed for alkylation of N,N-dialkylanilines with substituted β-nitrostyrenes using 10 mol% of choline chloride-zinc chloride deep eutectic solvent at 70 °C. The reaction was highly regioselective and only para-substituted products have been prepared. Despite the sensitivity and weak reactivity of the aniline derivatives for the Friedel–Crafts reaction in acidic media, the presented procedure was successfully carried out this transformation. The synthetic protocol was expanded for the alkylation of pyrrole and indole to produce pharmaceutically active compounds. The reduction of the nitro group of the product to amine was performed using Pd/C and hydrazine to produce amphetamine structure.

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References

  1. G.Y. Bai, H.Y. Dou, M. De Qiu, F. He, X.X. Fan, Z. Ma, Res. Chem. Intermed. 36, 483 (2010)

    Article  CAS  Google Scholar 

  2. K.M. Mesa, H.A. Hibbard, A.K. Franz, Org. Lett. 21, 3877 (2019)

    Article  CAS  PubMed  Google Scholar 

  3. A. Das, N. Anbu, A. Dhakshinamoorthy, S. Biswas, Inorg. Chem. 58, 5163 (2019)

    Article  CAS  PubMed  Google Scholar 

  4. C. Parida, R. Maity, S. Chandra-Sahoo, S. Chandra-Pan, Org. Lett. 21, 6700 (2019)

    Article  CAS  PubMed  Google Scholar 

  5. L. Qi, Russ. J. Org. Chem. 56, 169 (2020)

    Article  CAS  Google Scholar 

  6. T.B. Poulsen, K.A. Jørgensen, Chem. Rev. 108, 2903 (2008)

    Article  CAS  PubMed  Google Scholar 

  7. H. Wu, T. Zhao, X. Hu, Scientific Reports 8, 11449 (2018)

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  8. S. Chakraborty, H.C. You, C.K. Huang, B.Z. Lin, C.L. Wang, M.C. Tsai, C.Y. Lin, J. Phys. Chem. C 121, 7081 (2017)

    Article  CAS  Google Scholar 

  9. K. Aravindu, H.J. Kim, M. Taniguchi, P.L. Dilbeck, J.R. Diers, D.F. Bocian, J.S. Lindsey, Photochem. Photobiol. Sci. 12, 2089 (2013)

    Article  CAS  PubMed  Google Scholar 

  10. S.V. Goswami, P.B. Thorat, M.V. Shukla, S.R. Bhusare, Res. Chem. Intermed. 41, 2583 (2015)

    Article  CAS  Google Scholar 

  11. Y.M. Chung, Res. Chem. Intermed. 44, 3673 (2018)

    Article  CAS  Google Scholar 

  12. M. Beller, O.R. Thiel, H. Trauthwein, Synlett 1999, 243 (1999)

    Article  Google Scholar 

  13. K. Tanaka, K. Sakuragi, H. Ozaki, Y. Takada, Chem. Commun. 54, 6328 (2018)

    Article  CAS  Google Scholar 

  14. X. Hu, D. Martin, M. Melaimi, G. Bertrand, J. Am. Chem. Soc. 136, 13594 (2014)

    Article  CAS  PubMed  Google Scholar 

  15. R. Ballini, M. Petrini, Adv. Synth. Catal. 357, 2371 (2015)

    Article  CAS  Google Scholar 

  16. D. Markad, S.K. Mandal, ACS Catal. 9, 3165 (2019)

    Article  CAS  Google Scholar 

  17. M. Mu, L. Chen, Y. Liu, W. Fang, Y. Li, RSC Adv. 4, 36951 (2014)

    Article  CAS  Google Scholar 

  18. A. Perrier, M. Keller, A.M. Caminade, J.P. Majoral, A. Ouali, Green Chem. 15, 2075 (2013)

    Article  CAS  Google Scholar 

  19. A. Kumar, R.D. Shukla, D. Yadav, L.P. Gupta, RSC Advances 5, 52062 (2015)

    Article  CAS  Google Scholar 

  20. A.E. Ünlü, A. Arıkaya, S. Takaç, Green Process. Synthesis 8, 355 (2019)

    Article  CAS  Google Scholar 

  21. R. Aryan, H. Beyzaei, M. Nojavan, M. Rezaei, Res. Chem. Intermed. 43, 4731 (2017)

    Article  CAS  Google Scholar 

  22. A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, V. Tambyrajah, Green Chem. 4, 24 (2002)

    Article  CAS  Google Scholar 

  23. N. Azizi, E. Batebi, Catal. Sci. Technol. 2, 2445 (2012)

    Article  CAS  Google Scholar 

  24. A. Wang, P. Xing, X. Zheng, H. Cao, G. Yang, X. Zheng, RSC Adv. 5, 59022 (2015)

    Article  CAS  Google Scholar 

  25. D. Shahabi, H. Tavakol, J. Mol. Liq. 220, 324 (2016)

    Article  CAS  Google Scholar 

  26. F. Keshavarzipour, H. Tavakol, Catal. Lett. 145, 1062 (2015)

    Article  CAS  Google Scholar 

  27. H. Tavakol, F. Keshavarzipour, Appl. Organomet. Chem. 31, e3811 (2017)

    Article  CAS  Google Scholar 

  28. T. Ema, Y. Nanjo, S. Shiratori, Y. Terao, R. Kimura, Org. Lett. 18, 5764 (2016)

    Article  CAS  PubMed  Google Scholar 

  29. M. Takahashi, H. Koizumi, W.J. Chun, M. Kori, T. Imaoka, K. Yamamoto, Sci. Adv. 3, e1700101 (2017)

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  30. M. Tavakolian, S. Vahdati-Khajeh, S. Asgari, ChemCatChem 11, 2943 (2019)

    Article  CAS  Google Scholar 

  31. T. Murata, M. Hiyoshi, M. Ratanasak, J.Y. Hasegawa, T. Ema, Chem. Commun. 56, 5783 (2020)

    Article  CAS  Google Scholar 

  32. M. Zheng, Y. Wang, P. Feng, Catalysts 10, 309 (2020)

    Article  CAS  Google Scholar 

  33. M.K. Foumeshi, A.Z. Halimehjani, H. Paghandeh, P. Beier, Tetrahedron Lett. 61, 152270 (2020)

    Article  CAS  Google Scholar 

  34. A.Z. Halimehjani, M.V. Farvardin, H.P. Zanussi, M.A. Ranjbari, M. Fattahi, J. Mol. Catal. A: Chem. 381, 21 (2014)

    Article  CAS  Google Scholar 

  35. H. Wu, W.J. Sheng, B. Chen, R.R. Liu, J.R. Gao, Y.X. Jia, Synlett 26, 2817 (2015)

    Article  CAS  Google Scholar 

  36. W.A. Zuccarello, B. Blank, G.J. Frishmuth, S.R. Cohen, D. Scaricaciottoli, F.F. Owings, J. Med. Chem. 12, 9 (1969)

    Article  CAS  PubMed  Google Scholar 

  37. N. Yasukawa, M. Kuwata, T. Imai, Y. Monguchi, H. Sajiki, Y. Sawama, Green Chem. 20, 4409 (2018)

    Article  CAS  Google Scholar 

  38. D. Petruzziello, A. Gualandi, S. Grilli, P.G. Cozzi, Eur. J. Org. Chem. 2012, 6697 (2012)

    Article  CAS  Google Scholar 

  39. R.J. Tang, T. Milcent, B. Crousse, RSC Adv. 8, 10314 (2018)

    Article  CAS  Google Scholar 

  40. N. Yokoyama, T. Arai, Chem. Commun. 22, 3285 (2009)

    Article  CAS  Google Scholar 

  41. K. Firouz-Tadavani, A. Abdolmaleki, M.R. Molavian, M. Zhiani, ACS Appl. Energy Mater. 1, 2464 (2018)

    Article  CAS  Google Scholar 

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Acknowledgement

This work has been supported by Isfahan University of Technology.

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Correspondence to Hossein Tavakol.

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Ranjbari, M.A., Tavakol, H. & Manoukian, M. Regioselective and solvent-free arylation of β-nitrostyrenes with mono- and dialkyl anilines. Res Chem Intermed 47, 709–721 (2021). https://doi.org/10.1007/s11164-020-04294-6

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  • DOI: https://doi.org/10.1007/s11164-020-04294-6

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