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An efficient synthesis of polyfunctionalized pyrroles by three-component reaction of arylglyoxals, Meldrum’s acid and ethyl 2-chloro-3-(arylamino)but-2-enoates

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Abstract

A fast and convenient method for synthesis of some new functionalized pyrrole derivatives have been described via a three-component reaction between arylglyoxals, Meldrum’s acid and ethyl 2-chloro-3-(arylamino)but-2-enoate derivatives in excellent yields. When a mixture of arylglyoxal, Meldrum’s acid and ethyl 2-chloro-3-(arylamino)but-2-enoats were stirred in ethanol as a green solvent at room temperature, after one hour a solid product was separated from the reaction mixture. Simple filtration of this solid and its washing with ethanol afforded pure products. The structure of the products was proved by elemental analysis and IR and NMR apectral data.

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References

  1. S.S. Gholap, Eur. J. Med. Chem 110, 13 (2016)

    Article  CAS  Google Scholar 

  2. H. Fan, J. Peng, M.T. Hamann, J.F. Hu, Chem. Rev. 108, 264 (2008)

    Article  CAS  Google Scholar 

  3. R.W. Bürli, D. McMinn, J.A. Kaizerman, W. Hu, Y. Ge, Q. Pack, V. Jiang, M. Gross, M. Garcia, R. Tanaka, H.E. Moser, Bioorg. Med. Chem. Lett. 14, 1253 (2004)

    Article  Google Scholar 

  4. M.N. Narule, M.K. Gaidhane, P.K. Gaidhane, J. Pharm. Res. 6, 626 (2013)

    CAS  Google Scholar 

  5. C. Battilocchio, G. Poce, S. Alfonso, G.C. Porretta, S. Consalvi, L. Sautebin, S. Pace, A. Rossi, C. Ghelardini, L.D.C. Mannelli, S. Schenone, Bioorg. Med. Chem. 21, 3695 (2013)

    Article  CAS  Google Scholar 

  6. S.D. Joshi, S.R. Dixit, M.N. Kirankumar, T.M. Aminabhavi, K.V.S.N. Raju, R. Narayan, C. Lherbet, K.S. Yang, Eur. J. Med. Chem. 107, 133 (2016)

    Article  CAS  Google Scholar 

  7. A. Kamal, G. Ramakrishna, V.L. Nayak, P. Raju, A.S. Rao, A. Viswanath, M.V.P.S. Vishnuvardhan, S. Ramakrishna, G. Srinivas, Bioorg. Med. Chem. 20, 789 (2012)

    Article  CAS  Google Scholar 

  8. M.W. Roomi, S.F. MacDonald, Can. J. Chem. 48, 1689 (1970)

    Article  CAS  Google Scholar 

  9. F. Bonnaterre, M. Bois-Choussy, J. Zhu, Org. Lett. 8, 4351 (2006)

    Article  CAS  Google Scholar 

  10. B. Wang, Y. Gu, C. Luo, T. Yang, L. Yang, J. Suo, Tetrahedron Lett. 45, 3369 (2004)

    Article  CAS  Google Scholar 

  11. V. Estévez, M. Villacampa, J.C. Menéndez, Chem. Soc. Rev. 43, 4633 (2014)

    Article  Google Scholar 

  12. D. Tzankova, S. Vladimirova, L. Peikova, M. Georgieva, J. Chem. Tech. Matallurgy 53, 451 (2018)

    CAS  Google Scholar 

  13. A. Sharma, P. Piplani, J. Heterocycl. Chem. 54, 27 (2017)

    Article  CAS  Google Scholar 

  14. R.A. Jones, G.P. Bean, J. Heterocycl. Chem. 34, 27 (2013)

    Google Scholar 

  15. V. Bhardwaj, D. Gumber, V. Abbot, S. Dhiman, P. Sharma, RSC Adv. 5, 15233 (2015)

    Article  CAS  Google Scholar 

  16. M. Bayat, S. Nasri, B. Notash, Tetrahedron 73, 1522 (2017)

    Article  CAS  Google Scholar 

  17. X.B. Chen, Z.C. Liu, L.F. Yang, S.J. Yan, J. Lin, ACS Sustain Chem. Eng. 2, 1155 (2014)

    Article  CAS  Google Scholar 

  18. D.J. Viradiya, B.H. Baria, R. Kakadiya, V.C. Kotadiya, Int. Lett. Chem Phy. Astro. 11, 257 (2014)

    Article  Google Scholar 

  19. H. Wang, X. Liu, X. Feng, Z. Huang, D. Shi, GAP Green Chem. 15, 3307 (2013)

    Article  CAS  Google Scholar 

  20. S. Ambethkar, V. Padmini, N. Bhuvanesh, New J. Chem. 40, 4705 (2016)

    Article  CAS  Google Scholar 

  21. R. Mishra, A.K. Panday, L.H. Choudhury, J. Pal, R. Subramanian, A. Verma, Chem. Eur. J. 19, 2789 (2017)

    Article  Google Scholar 

  22. J. Wei, L. Liu, D.N. Tang, C.P. Wu, X.J. Zhao, W.J. Hao, B. Jiang, J. Heterocycl. Chem. 54, 3403 (2017)

    Article  CAS  Google Scholar 

  23. M. Ghandi, A. Jourablou, A. Abbasi, J. Heterocycl. Chem. 54, 3108 (2017)

    Article  CAS  Google Scholar 

  24. S. Karamthulla, A. Jana, L.H. Choudhury, ACS Comb Sci. 19, 108 (2017)

    Article  CAS  Google Scholar 

  25. N.N. Man, J.Q. Wang, L.M. Zhang, L.R. Wen, M. Li, J. Org. Chem. 82, 5566 (2017)

    Article  CAS  Google Scholar 

  26. I. Dhinakaran, V. Padmini, N. Bhuvanesh, ACS Comb Sci. 18, 236 (2016)

    Article  CAS  Google Scholar 

  27. M. Anary-Abbasinejad, M. Talebizadeh, J. Iran. Chem. Soc. 11, 963 (2014)

    Article  CAS  Google Scholar 

  28. F. Mousavizadeh, M. Talebizadeh, M. Anary-Abbasinejad, Tetrahedron Lett. 59, 2970 (2018)

    Article  CAS  Google Scholar 

  29. M. Masoudi, M. Anary-Abbasinejad, Tetrahedron Lett. 57, 103 (2016)

    Article  CAS  Google Scholar 

  30. H.A. Riley, A.R. Gray, Organic Synthesis (Wiley, New York, 1943)

    Google Scholar 

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The funding was provided by vali-e-asr university of rafsanjan

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Correspondence to Mohammad Anary-Abbasinejad.

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Nezhad-shahrokhabadi, F., Anary-Abbasinejad, M. An efficient synthesis of polyfunctionalized pyrroles by three-component reaction of arylglyoxals, Meldrum’s acid and ethyl 2-chloro-3-(arylamino)but-2-enoates. J IRAN CHEM SOC 19, 2655–2661 (2022). https://doi.org/10.1007/s13738-021-02485-5

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