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l-Tryptophan-catalyzed Paal–Knorr pyrrole cyclocondensation: an efficient, clean and recyclable organocatalyst

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Abstract

A simple, clean, and efficient solvent-free protocol is introduced for Paal–Knorr pyrrole synthesis catalyzed by l-tryptophan as a thermally resistant, natural primary amino acid. The products were obtained mostly in excellent yields through the reaction of hexane-2,5-dione with aromatic primary amines bearing a variety of substituents. The catalyst could be easily isolated from the reaction mixture and recycled at least six times without significant loss of activity. The procedure has an environmentally benign nature in agreement with the concepts of green chemistry.

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References

  1. A. Fürstner, H. Szillat, B. Gabor, R. Mynott, J. Am. Chem. Soc. 120, 8305–8314 (1998)

    Article  Google Scholar 

  2. P.A. Jacobi, L.D. Coutts, J. Guo, S.I. Hauck, S.H. Leung, J. Org. Chem. 65, 205–213 (2000)

    Article  CAS  Google Scholar 

  3. A. Fürstner, Angew. Chem. Int. Ed. 42, 3582–3603 (2003)

    Article  Google Scholar 

  4. V.F. Ferreira, M.C.B.V. De Souza, A.C. Cunha, L.O.R. Pereira, M.L.G. Ferreira, Org. Prep. Proced. Int. 33, 411–454 (2001)

    Article  CAS  Google Scholar 

  5. G. Minetto, L.F. Raveglia, M. Taddei, Org. Lett. 6, 389–392 (2004)

    Article  CAS  Google Scholar 

  6. U. Joshi, M. Pipelier, S. Naud, D. Dubreuil, Curr. Org. Chem. 9, 261–288 (2005)

    Article  CAS  Google Scholar 

  7. F.-P. Ma, P.-H. Li, B.-L. Li, L.-P. Mo, N. Liu, H.-J. Kang, Y.-N. Liu, Z.-H. Zhang, Appl. Catal. A Chem. 457, 34–41 (2013)

    Article  CAS  Google Scholar 

  8. B.-L. Li, H.-C. Hu, L.-P. Mo, Z.-H. Zhang, RSC Adv. 4, 12929–12943 (2014)

    Article  CAS  Google Scholar 

  9. H.-C. Hu, Y.-H. Liu, B.-L. Li, Z.-S. Cui, Z.-H. Zhang, RSC Adv. 5, 7720–7728 (2015)

    Article  CAS  Google Scholar 

  10. B.K. Banik, I. Banik, M. Renteria, S.K. Dasgupta, Tetrahedron Lett. 46, 2643–2645 (2005)

    Article  CAS  Google Scholar 

  11. J. Chen, H. Wu, Z. Zheng, C. Jin, X. Zhang, W. Su, Tetrahedron Lett. 47, 5383–5387 (2006)

    Article  CAS  Google Scholar 

  12. Z.-H. Zhang, J.-J. Li, T.-S. Li, Ultrason. Sonochem. 15, 673–676 (2008)

    Article  CAS  Google Scholar 

  13. J.-X. Chen, M.-C. Liu, X.-L. Yang, J.-C. Ding, H.-Y. Wu, J. Braz. Chem. Soc. 19, 877–883 (2008)

    Article  CAS  Google Scholar 

  14. A.A. Jafari, H. Mahmoudi, Environ. Chem. Lett. 11, 157–162 (2013)

    Article  CAS  Google Scholar 

  15. M. Curini, F. Montanari, O. Rosati, E. Lioy, R. Margarita, Tetrahedron Lett. 44, 3923–3925 (2003)

    Article  CAS  Google Scholar 

  16. B.K. Banik, S. Samajdar, I. Banik, J. Org. Chem. 69, 213–216 (2004)

    Article  CAS  Google Scholar 

  17. M. Abid, A. Spaeth, B. Török, Adv. Synth. Catal. 348, 2191–2196 (2006)

    Article  CAS  Google Scholar 

  18. A. Teimouri, A.N. Chermahini, Chin. J. Chem. 30, 372–376 (2012)

    Article  CAS  Google Scholar 

  19. N.T.S. Phan, T.T. Nguyen, Q.H. Luu, L.T.L. Nguyen, J. Mol. Catal. A Chem. 363–364, 178–185 (2012)

    Article  Google Scholar 

  20. L. Gao, L. Bing, Z. Zhang, H. Kecheng, H. Xiaoyun, K. Deng, J. Organomet. Chem. 735, 26–31 (2013)

    Article  CAS  Google Scholar 

  21. S. Cheraghi, D. Saberi, A. Heydari, Catal. Lett. 144, 1339–1343 (2014)

    Article  CAS  Google Scholar 

  22. B. Wang, Y. Gu, C. Luo, T. Yang, L. Yang, J. Suo, Tetrahedron Lett. 45, 3417–3419 (2004)

    Article  CAS  Google Scholar 

  23. J.S. Yadav, B.V.S. Reddy, B. Eeshwaraiah, M.K. Gupta, Tetrahedron Lett. 45, 5873–5876 (2004)

    Article  CAS  Google Scholar 

  24. S. Handy, K. Lavender, Tetrahedron Lett. 54, 4377–4379 (2013)

    Article  CAS  Google Scholar 

  25. H. Zheng, Q. Shi, K. Du, Y. Mei, P. Zhang, Mol. Divers. 17, 245–250 (2013)

    Article  CAS  Google Scholar 

  26. N. Azizi, A. Davoudpour, F. Eskandari, E. Batebi, Monatsh. Chem. 144, 405–409 (2013)

    Article  CAS  Google Scholar 

  27. S. Menuel, J. Rousseau, C. Rousseau, E. Vaiciunaite, J. Dodonova, S. Tumkevicius, E. Monflier, Eur. J. Org. Chem. 20, 4356–4361 (2014)

  28. E.L. Gibson, K. Vargas, E. Hogan, A. Holmes, P.J. Rogers, J. Wittwer, J. Kloek, R. Goralczyk, M.H. Mohajeri, Psychopharmacology 231, 4595–4610 (2014)

    Article  CAS  Google Scholar 

  29. L. Nyeste, M. Pécs, B. Sevella, J. Holló, Adv. Biochem. Eng. Biotech. 26, 175–202 (1983)

    CAS  Google Scholar 

  30. P. Kumar, N. Dwivedi, Acc. Chem. Res. 46, 289–299 (2013)

    Article  CAS  Google Scholar 

  31. L.-W. Xu, Y. Lu, Org. Biomol. Chem. 6, 2047–2053 (2008)

    Article  CAS  Google Scholar 

  32. Z. Jiang, Z. Liang, X. Wu, Y. Lu, Chem. Commun. 26, 2801–2803 (2006)

  33. S.S.V. Ramasastry, H. Zhang, F. Tanaka, C.F. Barbas III, J. Am. Chem. Soc. 129, 288–289 (2007)

    Article  CAS  Google Scholar 

  34. Y. Hu, Y.-H. He, Z. Guan, Catal. Commun. 11, 656–659 (2010)

    Article  CAS  Google Scholar 

  35. H.R. Darabi, M.R. Poorheravi, K. Aghapoor, A. Mirzaee, F. Mohsenzadeh, N. Asadollahnejad, H. Taherzadeh, Y. Balavar, Environ. Chem. Lett. 10, 5–12 (2012)

    Article  CAS  Google Scholar 

  36. K. Aghapoor, L. Ebadi-Nia, F. Mohsenzadeh, M.M. Morad, Y. Balavar, H.R. Darabi, J. Organomet. Chem. 708–709, 25–30 (2012)

    Article  Google Scholar 

  37. H.R. Darabi, K. Aghapoor, A. Darestani, Farahani, F. Mohsenzadeh. Environ. Chem. Lett. 10, 369–375 (2012)

    Article  CAS  Google Scholar 

  38. H. Lee, B.H. Kim, Tetrahedron 69, 6698–6708 (2013)

    Article  CAS  Google Scholar 

  39. N.V.S. Rao, K.S. Rao, Proc. Indian Acad. Sci. Sect. A 73, 59–63 (1971)

    Google Scholar 

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Authors and Affiliations

  1. Applied Chemicals Synthesis Laboratory, Chemistry and Chemical Engineering Research Center of Iran, Pajoohesh Blvd., km 17, Karaj Hwy, 14968-13151, Tehran, Iran

    Kioumars Aghapoor, Farshid Mohsenzadeh, Hossein Reza Darabi, Hani Sayahi & Yadollah Balavar

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  1. Kioumars Aghapoor
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  2. Farshid Mohsenzadeh
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  3. Hossein Reza Darabi
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  4. Hani Sayahi
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  5. Yadollah Balavar
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Correspondence to Kioumars Aghapoor.

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Aghapoor, K., Mohsenzadeh, F., Darabi, H.R. et al. l-Tryptophan-catalyzed Paal–Knorr pyrrole cyclocondensation: an efficient, clean and recyclable organocatalyst. Res Chem Intermed 42, 407–415 (2016). https://doi.org/10.1007/s11164-015-2026-1

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  • DOI: https://doi.org/10.1007/s11164-015-2026-1

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