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Efficient and extremely facile one-pot four-component synthesis of mono and bis-N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates catalyzed by p-TsOH·H2O

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An Erratum to this article was published on 21 September 2013

Abstract

An efficient and straightforward procedure has been developed for synthesis of mono and bis-N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates via one-pot four-component domino reaction of amines, dialkyl acetylenedicarboxylates, and formaldehyde, in the presence of p-TsOH·H2O (15 mol%), in MeOH at ambient temperature. The salient advantages of this method are mild reaction conditions, high to excellent yields, shorter reaction times, atom economy, easy operation, and no column chromatographic separation.

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References

  1. M. Li, A.-X. Qiu, L.-R. Wen, Z.-M. Zhou, Tetrahedron 67, 3638 (2011)

    Article  CAS  Google Scholar 

  2. F. Balkenhohl, C. von dem Bussche-Hunnefeld, A. Lanshy, C. Zechel, Angew. Chem. Int. Ed. Engl. 35, 2289 (1996)

    Article  Google Scholar 

  3. T. Eicher, S. Hauptmann, The Chemistry of Heterocycles, 2nd edn. (Wiley, Weinheim, 2003)

    Book  Google Scholar 

  4. W.-J. Bai, S.K. Jakson, T.R.R. Pettus, Org. Lett. 14, 3862 (2012)

    Article  CAS  Google Scholar 

  5. M. Aginagalde, T. Bello, C. Masdeu, Y. Vara, A. Arrieta, F.P. Cossío, J. Org. Chem. 75, 7435 (2010)

    Article  CAS  Google Scholar 

  6. I. Loke, N. Park, K. Kempf, C. Jagusch, R. Schobert, S. Laschat, Tetrahedron 68, 697 (2012)

    Article  CAS  Google Scholar 

  7. Y. Zhao, Q. Wang, Q. Meng, D. Ding, H. Yang, G. Gao, D. Li, W. Zhu, H. Zhou, Bioorg. Med. Chem. 20, 1240 (2012)

    Article  CAS  Google Scholar 

  8. M. Hosseini, H. Kringelum, A. Murray, J.E. Tønder, Org. Lett. 8, 2103 (2006)

    Article  CAS  Google Scholar 

  9. L. Ettlinger, E. Gäuemann, R. Hütter, W. Keller-Schierlein, F. Kradolfer, L. Neipp, V. Prelog, H. Zähner, Helv. Chim. Acta 42, 563 (1959)

    Article  CAS  Google Scholar 

  10. H. Shiozawa, S. Takahashi, J. Antibiot. 47, 851 (1994)

    Article  CAS  Google Scholar 

  11. S.B. Singh, M.A. Goetz, E.T. Jones, G.F. Bills, R.A. Giacobbe, L. Herranz, S. Stevens-Miles, D.L. Williams Jr, J. Org. Chem. 60, 7040 (1995)

    Article  CAS  Google Scholar 

  12. B.L. Mylari, T.A. Beyer, T.W. Siegel, J. Med. Chem. 34, 1011 (1991)

    Article  CAS  Google Scholar 

  13. H. He, H.Y. Yang, R. Bigelis, E.H. Solum, M. Greenstein, G.T. Carter, Tetrahedron Lett. 43, 1633 (2002)

    Article  CAS  Google Scholar 

  14. T. Sasaki, S. Takahashi, K. Uchida, S. Funayama, M. Kainosho, A. Nakagawa, J. Antibiot. 59, 418 (2006)

    Article  CAS  Google Scholar 

  15. J. Chen, P.-Q. Huang, Y. Queneau, J. Org. Chem. 74, 7457 (2009)

    Article  CAS  Google Scholar 

  16. A. Raghuraman, E. Ko, L.M. Perez, T.R. Loerger, K. Burgess, J. Am. Chem. Soc. 133, 12350 (2011)

    Article  CAS  Google Scholar 

  17. T. Kawasuji, M. Fuji, T. Yoshinaga, A. Sato, T. Fujiwarab, R. Kiyamaa, Bioorg. Med. Chem. 15, 5487 (2007)

    Article  CAS  Google Scholar 

  18. L. Zhang, Y. Tan, N.-X. Wang, Q.-Y. Wu, Z. Xi, G.-F. Yang, Bioorg. Med. Chem. 18, 7948 (2010)

    Article  CAS  Google Scholar 

  19. R. Fischer, S. Lehr, M. W. Drewes, D. Feucht, O. Malsam, G. Bojack, C. Arnold, T. Auler, M. Hills, H. Kehne, German Patent DE 102004053191, 2006

  20. B. Li, M.P.A. Lyle, G. Chen, J. Li, K. Hu, L. Tang, M.A. Alaoui-Jamali, J. Webster, Bioorg. Med. Chem. 15, 4601 (2007)

    Article  CAS  Google Scholar 

  21. A.S. Demir, F. Aydigan, I.M. Akhmedov, Tetrahedron 13, 601 (2002)

    Article  CAS  Google Scholar 

  22. S. Kiren, X. Hong, C.A. Leverett, A. Padwa, Tetrahedron 65, 6720 (2009)

    Article  CAS  Google Scholar 

  23. C. Alp, D. Ekinci, M.S. Gültekin, M. Şentürk, E. Şahin, Öİ. Küfrevioğlu, Bioorg. Med. Chem. 18, 4468 (2010)

    Article  CAS  Google Scholar 

  24. D. Albrecht, B. Basler, T. Bach, J. Org. Chem. 73, 2345 (2008)

    Article  CAS  Google Scholar 

  25. I. Dias-Jurberg, F. Gagosz, S.Z. Zard, Org. Lett. 12, 416 (2010)

    Article  CAS  Google Scholar 

  26. T. Sengoku, Y. Nagae, Y. Ujihara, M. Takahashi, H. Yoda, J. Org. Chem. 77, 4391 (2012)

    Article  CAS  Google Scholar 

  27. Q. Zhu, H. Jiang, J. Li, S. Liu, C. Xia, M. Zhang, J. Comb. Chem. 11, 685 (2009)

    Article  CAS  Google Scholar 

  28. A.T. Khan, A. Ghosh, Md. M. Khan. Tetrahedron Lett. 53, 2622 (2012)

    Article  CAS  Google Scholar 

  29. H. Gao, J. Sun, C.-G. Yan, Tetrahedron 69, 589 (2013)

    Article  CAS  Google Scholar 

  30. S. Rana, M. Brown, A. Dutta, A. Bhaumik, C. Mukhopadhyay, Tetrahedron Lett. 54, 1371 (2013)

    Article  CAS  Google Scholar 

  31. Q. Zhu, L. Gao, Z. Chen, S. Zheng, H. Shu, J. Li, H. Jiang, S. Liu, Eur. J. Med. Chem. 54, 232 (2012)

    Article  CAS  Google Scholar 

  32. Y. Han, Q. Wu, J. Sun, C.-G. Yan, Tetrahedron 68, 8539 (2012)

    Article  CAS  Google Scholar 

  33. S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, K. Khandan-Barani, J. Chem. Res. 37, 40 (2013)

    Article  CAS  Google Scholar 

  34. S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, A.C. Willis, J. Iran. Chem. Soc. (2013). doi:10.1007/s13738-013-0222-8

    Google Scholar 

  35. S.S. Sajadikhah, N. Hazeri, Res. Chem. Intermed. (2013). doi:10.1007/s11164-012-0998-7

    Google Scholar 

  36. S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, J. Chin. Chem. Soc. 60, 1003 (2013)

    Google Scholar 

  37. N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, G. Marandi, Arkivoc xiv, 282 (2008)

    Article  Google Scholar 

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Acknowledgments

We are grateful to the Research Council of University of Sistan and Baluchestan for financial support of this work.

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Correspondence to Seyed Sajad Sajadikhah.

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Sajadikhah, S.S., Maghsoodlou, M.T. & Hazeri, N. Efficient and extremely facile one-pot four-component synthesis of mono and bis-N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates catalyzed by p-TsOH·H2O. Res Chem Intermed 41, 2503–2511 (2015). https://doi.org/10.1007/s11164-013-1364-0

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