JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 63 No 1 (2018): Journal of the Chilean Chemical Society
Original Research Papers

TRIFLUOROACETIC ACID CATALYZED ONE-POT FOUR-COMPONENT DOMINO REACTION FOR THE SYNTHESIS OF SUBSTITUTED DIHYDRO 2-OXYPYRROLES

Mojtaba Lashkari
Faculty of Science, Velayat University, Iranshahr.
Malek Taher Maghsoodlou
Department of Chemistry, University of Sistan and Baluchestan, Zahedan.
Mahsa Karima
Department of Chemistry, University of Sistan and Baluchestan, Zahedan.
Mehrnoosh Kangani
Department of Chemistry, University of Sistan and Baluchestan, Zahedan.
Published April 25, 2018
Keywords
  • Trifluoroacetic acid,
  • N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates,
  • ambient temperature
How to Cite
Lashkari, M., Taher Maghsoodlou, M., Karima, M., & Kangani, M. (2018). TRIFLUOROACETIC ACID CATALYZED ONE-POT FOUR-COMPONENT DOMINO REACTION FOR THE SYNTHESIS OF SUBSTITUTED DIHYDRO 2-OXYPYRROLES. Journal of the Chilean Chemical Society, 63(1). Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/575

Abstract

Trifluoroacetic acid was applied as an efficient catalyst for the one-pot four-component synthesis of N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates via the domino reaction of amines, formaldehyde and dialkyl acetylenedicarboxylates at ambient temperature in methanol. This methodology includes number of advantages such as: short reaction time, clean work-up, use of inexpensive catalyst, high yields and clean work-up. The work-up of this reaction involves only a filtration and a simple washing step with MeOH, and there is no need for column chromatography.

References

  1. T. Eicher, S. Hauptmann, Wiley-VCH, Weinheim, (2003).
  2. P.Z. Zhang, S.F. Zhou, T.R. Li, L. Jiang, Chin. Chem. Lett. 23, 1381 (2012).
  3. T.N. Akhaja, J.P. Raval, Design, Chin. Chem. Lett. 23, 446 (2012).
  4. W.J. Bai, S.K. Jakson, T.R.R. Pettus, Org. Lett. 14, 3862 (2012).
  5. M. Aginagalde, T. Bello, C. Masdeu, Y.Vara, A. Arrieta, F. Cossío J. Org. Chem. 75, 7435 (2010).
  6. H. Anaraki-Ardakani, M. Noei, A. Tabarzad, Chin. Chem. Lett. 23, 45 (2012).
  7. L. Ettlinger, E. Ga¨uemann, R. Hu¨tter, W. Keller-Schierlein, F. Kradolfer, L. Neipp, V. Prelog, H. Zähner, Helv. Chim. Acta 42, 563 (1959).
  8. H. Shiozawa, S. Takahashi, J. Antibiot. 47, 851 (1994).
  9. S.B. Singh, M.A. Goetz, E.T. Jones, G. F. Bills, R. A. Giacobbe, L.H. Siobhan Stevens- Miles, D. L. Williams, J. Org. Chem. 60, 7040 (1995).
  10. H. He, H.Y. Yang, R. Bigelis, E. H. Solum, M. Greenstein, Tetrahedron Lett. 43, 1633 (2002).
  11. A.J. Clark, C.P. Dell, J.M. McDonagh, J. Geden, P. Mawdsley, Org. Lett. 5, 2063 (2003).
  12. J. Chen, P.Q. Huang, Y. Queneau, J. Org. Chem. 74, 7457 (2009).
  13. A. Raghuraman, E. Ko, L.M. Perez, T. R. Ioerger, K. Burgess, J. Am. Chem. Soc. 133, 12350 (2011).
  14. T. Kawasuji, M. Fuji, T. Yoshinaga, A. Sato, T. Fujiwara, R. Kiyama, Bioorg. Med. Chem. 15, 5487 (2007).
  15. L. Zhang, Y. Tan, N.X. Wang, Q.Y. Wu, Z. Xi, G.F. Yang, Bioorg. Med. Chem. 18, 7948 (2010).
  16. Y. Mizushina, S. Kobayashi, K. Kuramochi, S.Nagata, F. Sugawara, K. Sakaguchi, Biochem.Biophys. Res. Commun. 273, 784 (2000).
  17. Q. Zhu, L. Gao, Z. Chen, S. Zheng, H. Shu, J. Liet, Eur. J. Med. Chem. 54, 232 (2012).
  18. B. Li, M.P.A. Lyle, G. Chen, J. Li, K. L. T. Hu, M. A. Alaoui-Jamali, J. Webster, Bioorg. Med. Chem. 15, 4601 (2007).
  19. A.S. Demir, F. Aydigan, I.M. Akhmedov, Tetrahedron: Asymmetry 13, 601 (2002).
  20. T.R.K. Reddy, C. L, X. Guo, X. Myrvang, H.K. P. M. Fischer, L. V. Dekker, J. Med. Chem. 54, 2080 (2011).
  21. Q. Zhu, H. Jiang, J. Li, S. Liu, C. Xia, M. Zhang, J. Comb. Chem. 11, 685 (2009).
  22. A.T. Khan, A. Ghosh, Md.M. Khan, Tetrahedron Lett. 53, 2622 (2012).
  23. H. Gao, J. Sun, C.G. Yan, Tetrahedron 69, 589 (2013).
  24. S. Rana, M. Brown, A. Dutta, A. Bhaumik, C. Mukhopadhyay, Tetrahedron Lett. 54, 1371 (2013).
  25. L. Lv, S. Zheng, X. Cai, Z. Chen, Q. Zhu, S. Liu, ACS Comb. Sci. 15, 183 (2013).
  26. R. Doostmohammadi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi- Khorassani, Res. Chem. Intermed., 38, 4061 (2012).
  27. S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S. M. Habibi-Khorassani, A.C. Willis, Chin. Chem. Lett. 23, 569 (2012).
  28. M.T. Maghsoodlou, S.M. Habibi-Khorasani, Z. Shahkarami, N. Maleki, M. Rostamizadeh, Chem. Lett. 21, 686 (2010).
  29. S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, A.C. Willis, J. Iran. Chem. Soc. 10, 863 (2013).
  30. S.S. Sajadikhah, N. Hazeri, Res. Chem. Int. 40, 737(2014).
  31. S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, J. Chin. Chem. Soc. 60, 1003 (2013).
  32. For a review, see: (a) T. Wu, H. Yu, C. Li, ARKIVOC ix (2004) 60– 65; (b) P.E. Peterson, C. Casey, E.V.P. Tao, A. Agtarap, G. Thompson, J. Am. Chem. Soc. 87 (1965) 5163–5169; (c) P.E. Peterson, R.J. Bopp, D.M. Chevli, E.L. Curran, D.E. Dillard, R.J. Kamat, J. Am. Chem. Soc. 89 (1967) 5902–5911.
  33. (a) For a review, see: K. Turnbull, D.M. Krein, Synthesis (1999) 391–392; (b) R. Venkateswarlu, C. Kamakshi, P.V. Subhash, S.G.A. Moinuddin, M.P. Gowri, R.S. Ward, A. Pelter, M.B. Hursthouse, S.J. Coles, M.E. Light, Tetrahedron 61 (2005) 8956–8961; (c) A.M. Martin-Castro, Chem. Rev. 104 (2004) 2939–3002; (d) R. Pathak, S. Madapa, S. Batra, Tetrahedron 63 (2007) 451-460.
  34. For a review, see: (a) R.D. Wakharkar, M.B. Sahasrabuddhe, H.B. Borate, M.K. Gurjar, Synthesis (2004) 1830–1834; (b) V.V.N.K.V.P. Raju, V. Ravindra, S.S. Kamath, V.T. Mathad, P.K. Dubey, P.P. Reddya, ARKIVOC xii (2009) 296–301; (c) A.K. Singh, R.E. Weaver, G.L. Powers, V.W. Rosso, C. Wei, D.A. Lust, A.S. Kotnis, F.T. Comezoglu, M. Liu, K.S. Bembenek, B.D. Phan, D.J. Vanyo, M.L. Davies, R. Mathew, V.A. Palaniswamy, W.-S. Li, K. Gadamsetti, C.J. Spagnuolo, W.J. Winter, Org. Proc. Res. Dev. 7 (2003) 25–27.
  35. For a review, see: (a) S.A. Bowden, J.N. Burke, F. Gray, S. McKown, J.D. Moseley, W.O. Moss, P.M. Murray, M.J. Welham, M.J. Young, Org. Proc. Res. Dev. 8 (2004) 33-44; (b) G.T. Bourne, D.J. Kuster, G.R. Marshall, Chem. Eur. J. 16 (2010) 8439–8445; (c) R.N. Misra, D.B. Rawlins, H.- Y. Xiao, W. Shan, I. Bursuker, K.A. Kellar, J.G. Mulheron, J.S. Sack, J.S. Tokarski, S.D. Kimball, K.R. Webster, Bioorg. Med. Chem. Lett. 13 (2003) 1133–1136; (d) K.G. Akamanchi, N.R. Varalakshmy, B.A. Chaudhari, Synlett (1997) 371–372; (e) M.N. Masuno, T.F. Molinski, Tetrahedron Lett. 42 (2001) 8263–8266; (f) J.P. Patel, A.-H. Li, H. Dong, V.L. Korlipara, M.J. Mulvihill, Tetrahedron Lett. 50 (2009) 5975–5977.
  36. For a review, see: (a) A.A. Zagulyaeva, M.S. Yusubov, V.V. Zhdankin, J. Org. Chem. 75 (2010) 2119–2122; (b) G.A. Olah, Q. Wang, N.J. Trivedi, G.K.S. Prakash, Synthesis (1991) 739–740; (c) R.A. Kjonaas, A.E. Clemons, J. Chem. Ed. 85 (2008) 827–828.
  37. For a review, see: (a) K. Li, L.N. Foresee, J.A. Tunge, J. Org. Chem. 70 (2005) 2881–2883; (b) T. Hashimoto, S. Kutubi, T. Izumi, A. Rahman, T. Kitamura, J. Organometal. Chem. 696 (2011) 99–105.
  38. For a review, see: (a) M.R. Mohammadizadeh, A. Hasaninejad, M. Bahramzadeh, Synth. Commun. 39 (2009) 3232–3242; (b) J. Salazar, S.E. Lo´ pez, O. Rebollo, J. Fluorine Chem. 124 (2003) 111–113; (c) J. Ohtaka, T. Sakamoto, Y. Kikugawa, Tetrahedron Lett. 50 (2009) 1681–1683; (d) S.E. Lo´ pez, Y. Pe´ rez, J. Restrepo, J. Salazar, J. Charris, J. Fluorine Chem. 128 (2007) 566–569; (e) F. Herna´ ndez-Luis, A. Herna´ ndez- Campos, R. Castillo, G. Navarrete-Va´zquez, O. Soria-Arteche, M. Herna´ ndez-Herna´ ndez, L. Ye´pez-Mulia, L. Eur, J. Med. Chem. 45 (2010) 3135–3141.
  39. For a review, see: (a) X.-G. Zhang, H.-X. Dai, M. Wasa, J.-Q. Yu, J. Am. Chem. Soc. 134 (2012) 11948–11951; (b) M. Eisenberg, D.D. Desmarteau, Inorg. Nucl. Chem. Lett. 6 (1970) 29–34; (c) A. Gregoric, M. Zupan, J. Org. Chem. 44 (1979) 4120–4122; (d) T.B. Patrick, K.K. Johli, D.H. White, W.S. Bertrand, R. Mokhtar, M.R. Kilboourn, M.J. Welch, Can. J. Chem. 64 (1986) 138–141; (e) Y. Tanabe, N. Matsuo, N. Ohno, J. Org. Chem. 53 (1988) 4582–4585; (f) N.V. Kondratenko, E.P. Vechirko, L.M. Yagupolskii, Synthesis (1980) 932; (g) F. Cottet, M. Schlosse, Eur. J. Org. Chem. (2002) 327–330.
  40. S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, 2013, DOI 10.1007/ s11164-013-1364-0.
  41. H.-J. Wang, L.-P. Mo, Z.-H. Zhang, ACS Comb. Sci. 13, 181 (2011).
  42. S. Rana, M. Brown, A. Bhaumik, C. Mukhopadhyay. Tetrahedron Lett. 54 (2013) 1371-1379.
  43. S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, K. Khandan-Barani, J. Chem. Res., (2013) 40.
  44. S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, Chin. Chem. Lett., 25 (2014) 58.

Copyright @2019 | Designed by: Open Journal Systems Chile Logo Open Journal Systems Chile Support OJS, training, DOI, Indexing, Hosting OJS

Code under GNU license: OJS PKP