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Microwave assisted synthesis of dihydropyrrole by AgOAc catalyzed intramolecular cyclization reaction of homopropargyl amine

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Abstract

A series of 5-aryl dihydropyrrole was synthesized from the intramolecular cyclization reaction of homopropargyl amine in the presence of AgOAc as catalyst under microwave irradiation reaction conditions. The homopropargyl amine was prepared by the reaction of propargyl bromide with N-tosyl aldimine under a sonochemical Barbier-type reaction condition. Further aromatization reaction of 5-aryl dihydropyrrole in KOtBu/DMSO can afford 2-aryl pyrrole under microwave irradiation reaction conditions.

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Notes

  1. The addition of 1,2-diiodomoethane was used for the activation of metal, and it reacted with Zn powder in situ to generate Lewis acid ZnI2 and ethene.

  2. The ultrasonic cleaning bath (Elma-T490DH, 50 kHz) should be filled with water containing some 3–5 % detergent. In our laboratory, we used Decon 90, which permits much more even cavitation in bath water.

References

  1. R.J. Sundberg, in Comprehensive Heterocyclic Chemistry, vol. 4, ed. by A.R. Katritzky, C.W. Rees (Pergamon Press, Oxford, 1984), p. 313

    Chapter  Google Scholar 

  2. G.P. Bean, in Pyrroles, ed. by R.A. Jones (Wiley, New York, 1990), p. 105

    Google Scholar 

  3. R.J. Sundberg, in Comprehensive Heterocyclic Chemistry II, vol. 2, ed. by A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Elsevier, Oxford, 1996), p. 119

    Chapter  Google Scholar 

  4. G.W. Gribble, in Comprehensive Heterocyclic Chemistry II, vol. 2, ed. by A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Elsevier, Oxford, 1996), p. 207

    Chapter  Google Scholar 

  5. R.M. Baughman, J.L. Bredas, R.L. Elsenbaumer, L.W. Shacklette, Chem. Rev. 82, 209 (1982)

    Article  CAS  Google Scholar 

  6. R.D’. Alessio, A. Bargiotti, O. Carlini, F. Colotta, M. Ferrari, P. Gnocchi, A. Isetta, N. Mongelli, P. Motta, A. Rossi, M. Rossi, M. Tibolla, E. Vanotti, J. Med. Chem. 43, 2557 (2000)

    Article  Google Scholar 

  7. M.A. Galindo, J. Hannant, R.W. Harrington, W. Clegg, B.R. Horrocks, A.R. Pike, A. Houlton, Org. Biomol. Chem. 9, 1555 (2011)

    Article  CAS  Google Scholar 

  8. J.T. Gupton, Top Heterocycl. Chem. 2, 53 (2006)

    CAS  Google Scholar 

  9. M. Biava, G.C. Porretta, G. Poce, S. Supino, D. Deidda, R. Pompei, P. Molicotti, F. Manetti, M. Botta, J. Med. Chem. 49, 4946 (2006)

    Article  CAS  Google Scholar 

  10. R. Martin, A. Jäger, M. Böhl, S. Richter, R. Fedorov, D.J. Manstein, H.O. Gutzeit, H.J. Knölker, Angew. Chem. Int. Ed. 48, 8042 (2009)

    Article  CAS  Google Scholar 

  11. M.G. Thomas, M.D. Burkart, C.T. Walsh, Chem. Biol. 9, 171 (2002)

    Article  CAS  Google Scholar 

  12. J. Regourd, A.A. Ali, A. Thompson. J. Med. Chem. 50, 1528 (2007)

    Article  CAS  Google Scholar 

  13. D. Fehér, R.S. Barlow, P.S. Lorenzo, T.K. Hemscheidt, J. Nat. Prod. 2008, 71 (1970)

    Google Scholar 

  14. M. Rene, J. Anne, J.K. Hans, Synlett 19, 2795 (2011)

    Google Scholar 

  15. H. Yoshimura, K. Kikuchi, S. Hibi, K. Tagami, T. Satoh, T. Yamauchi, A. Ishibahi, K. Tai, T. Hida, N. Tokuhara, M. Nagai, J. Med. Chem. 43, 2929 (2000)

    Article  CAS  Google Scholar 

  16. C.P. Gonzalo, J.A. Pomposoa, J.A. Alduncin, M. Salsamendi, A.I. Mikhaleva, L.B. Krivdin, B.A. Trofimov, Electrochim. Acta 52, 4784 (2007)

    Article  Google Scholar 

  17. C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 4957 (2004)

    Article  Google Scholar 

  18. H. Shiraishi, T. Nishitani, S. Sakaguchi, Y. Ishii, J. Org. Chem. 63, 6234 (1998)

    Article  CAS  Google Scholar 

  19. X. Lin, Z. Mao, X. Dai, P. Lu, Y. Wang, Chem. Commun. 47, 6620 (2011)

    Article  CAS  Google Scholar 

  20. O.A. Attanasi, G. Favi, F. Mantellini, G. Moscatelli, S. Santeusanio, J. Org. Chem. 76, 2860 (2011)

    Article  CAS  Google Scholar 

  21. E. Ghabraie, S. Balalaie, M. Bararjanian, H.R. Bijanzadeh, F. Rominger, Tetrahedron 67, 5415 (2011)

    Article  CAS  Google Scholar 

  22. C.R. Reddy, M.D. Reddy, B. Srikanth, K.R. Prasad, Org. Biomol. Chem. 9, 6027 (2011)

    Article  CAS  Google Scholar 

  23. B.M. Trost, J.-P. Lumb, J.M. Azzarelli, J. Am. Chem. Soc. 133, 740 (2011)

    Article  CAS  Google Scholar 

  24. A.V. Gulevich, A.S. Dudnik, N. Chernyak, V. Gevorgyan, Chem. Rev. 113, 3084 (2013)

    Article  CAS  Google Scholar 

  25. H.C. Brown, U.R. Khire, G. Narla, U.S. Racherla, J. Org. Chem. 60, 544 (1995)

    Article  CAS  Google Scholar 

  26. A.S.-Y. Lee, S.-F. Chu, S.-H. Wang, Y.-T. Chang, Tetrahedron Lett. 45, 1551 (2004)

    Article  CAS  Google Scholar 

  27. A.S.-Y. Lee, K.-W. Tsao, Y.-T. Chang, S.-F. Chu, Tetrahedron Lett. 48, 6790 (2007)

    Article  CAS  Google Scholar 

  28. J.E. Baldwin, J. Chem. Soc. Chem. Commun. 734 (1976)

  29. A.S.-Y. Lee, Y.-T. Chang, F.-Y. Su, J. Chin. Chem. Soc. 61(2), 290 (2014)

    Article  CAS  Google Scholar 

  30. A.S.-Y. Lee, Y.-T. Chang, Tetrahedron Lett. 51, 3800 (2010)

    Article  CAS  Google Scholar 

  31. A.S.-Y. Lee, C.-H. Chung, S.-F. Chu, Y.-T. Chang, J. Chin. Chem. Soc. 56, 202 (2009)

    Article  CAS  Google Scholar 

  32. A.S.-Y. Lee, K.-W. Tsao, Y.-T. Chang, S.-F. Chu, J. Chin. Chem. Soc. 54(2), 519 (2007)

    Article  CAS  Google Scholar 

  33. A.S.-Y. Lee, Y.-T. Chang, S.-F. Chu, K.-W. Tsao, Tetrahedron Lett. 47, 7085 (2006)

    Article  CAS  Google Scholar 

  34. A.S.-Y. Lee, Y.-T. Chang, S.-H. Wang, S.-F. Chu, Tetrahedron Lett. 43, 8489 (2002)

    Article  CAS  Google Scholar 

  35. A.S.-Y. Lee, R.-Y. Cheng, O.-G. Pan, Tetrahedron Lett. 38, 443 (1997)

    Article  CAS  Google Scholar 

  36. A.S.-Y. Lee, W.-C. Dai, Tetrahedron 53, 859 (1997)

    Article  CAS  Google Scholar 

  37. H.M. Wisniewska, E.R. Jarvo, Chem. Sci. 2, 807 (2011)

    Article  CAS  Google Scholar 

  38. B.L. Hayes, Microwave Synthesis (CEM Publishing, London, 2002)

    Google Scholar 

  39. A.S.-Y. Lee, Y.-C. Wu, Y.-T. Chang, B.-C. Wang, Res. Chem. Intermed. 40(6), 2277 (2014)

    Article  CAS  Google Scholar 

  40. A.S.-Y. Lee, C.-H. Chung, Y.-T. Chang, P.-L. Chen, J. Appl. Sci. Eng. 15(3), 311 (2012)

    Google Scholar 

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Acknowledgments

We thank the National Science Council in Taiwan (NSC 101-2113-M-032-003) and Tamkang University for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Tamkang University, New Taipei, 25137, Taiwan

    Adam Shih-Yuan Lee, Szu-Huio Ma Lee & Yu-Ting Chang

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  1. Adam Shih-Yuan Lee
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  2. Szu-Huio Ma Lee
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  3. Yu-Ting Chang
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Correspondence to Adam Shih-Yuan Lee.

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Lee, A.SY., Lee, SH.M. & Chang, YT. Microwave assisted synthesis of dihydropyrrole by AgOAc catalyzed intramolecular cyclization reaction of homopropargyl amine. Res Chem Intermed 43, 3493–3503 (2017). https://doi.org/10.1007/s11164-016-2442-x

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