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Brønsted acid-catalyzed aza-Mannich reaction of N-Boc aminals: access to multifunctional rhodanine/hydantoin derivatives

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Abstract

An effective aza-Mannich reaction between olefinic rhodanines/hydantoins and N-Boc aminals catalyzed by Brønsted acid has been developed. Multifunctional rhodanine/hydantoin derivatives were obtained in 71–86% yields and an up to 95/5 Z/E ratio under mild conditions.

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References

  1. A.S. Shawali, Chem. Rev. 93, 2731–2777 (1993)

    Article  CAS  Google Scholar 

  2. A.T. Balaban, D.C. Oniciu, A.R. Katritzky, Chem. Rev. 104, 2777–2812 (2004)

    Article  CAS  Google Scholar 

  3. F.G. Gelalcha, Chem. Rev. 107, 3338–3361 (2007)

    Article  CAS  Google Scholar 

  4. D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 107, 5606–5655 (2007)

    Article  CAS  Google Scholar 

  5. L. Benhamou, E. Chardon, G. Lavigne, S. Bellemin-Laponnaz, V. Cesar, Chem. Rev. 111, 2705–2733 (2011)

    Article  CAS  Google Scholar 

  6. B. Eftekhari-Sis, M. Zirak, A. Akbari, Chem. Rev. 113, 2958–3043 (2013)

    Article  CAS  Google Scholar 

  7. L. Kiss, F. Fulop, Chem. Rev. 114, 1116–1169 (2014)

    Article  CAS  Google Scholar 

  8. F.C. Brown, Chem. Rev. 61, 463–521 (1961)

    Article  CAS  Google Scholar 

  9. S.P. Singh, S.S. Parmar, K. Raman, V.I. Stenberg, Chem. Rev. 81, 175–280 (1981)

    Article  CAS  Google Scholar 

  10. S.L. Johnson, D. Jung, M. Forino, Y. Chen, A. Satterthwait, D.V. Rozanov, A.Y. Strongin, M. Pellecchia, J. Med. Chem. 49, 27–30 (2006)

    Article  CAS  Google Scholar 

  11. S. Jabeen, T.J. Dines, R. Withnall, S.A. Leharne, B.Z. Chowdhry, Phys. Chem. Chem. Phys. 11, 7476–7483 (2009)

    Article  CAS  Google Scholar 

  12. T.K. Smith, B.L. Young, H. Denton, D.L. Hughes, G.K. Wagner, Bioorg. Med. Chem. Lett. 19, 1749–1752 (2009)

    Article  CAS  Google Scholar 

  13. J. Choi, Y. Ko, H.S. Lee, Y.S. Park, Y. Yang, S. Yoon, Eur. J. Med. Chem. 45, 193–202 (2010)

    Article  CAS  Google Scholar 

  14. C. Fan, M.D. Clay, M.K. Deyholos, J.C. Vederas, Bioorg. Med. Chem. 18, 2141–2151 (2010)

    Article  CAS  Google Scholar 

  15. V. Opletalova, J. Dolezel, K. Kralova, M. Pesko, J. Kunes, J. Jampilek, Molecules 16, 5207–5227 (2011)

    Article  CAS  Google Scholar 

  16. O. Zvarec, S.W. Polyak, W. Tieu, K. Kuan, H. Dai, D.S. Pedersen, R. Morona, L. Zhang, G.W. Booker, A.D. Abell, Bioorg. Med. Chem. Lett. 22, 2720–2722 (2012)

    Article  CAS  Google Scholar 

  17. T.N. Reddy, M. Ravinder, P. Bagul, K. Ravikanti, C. Bagul, J.B. Nanubolu, K. Srinivas, S.K. Banerjee, V.J. Rao, Eur. J. Med. Chem. 71, 53–66 (2014)

    Article  CAS  Google Scholar 

  18. S. Guiheneuf, L. Paquin, F. Carreaux, E. Durieu, T. Roisnel, L. Meijer, J.P. Bazureau, Mol. Divers. 18, 375–388 (2014)

    Article  CAS  Google Scholar 

  19. J. Brem, S.S. Berkel, W. Aik, A.M. Rydzik, M.B. Avison, I. Pettinati, K.D. Umland, A. Kawamura, J. Spencer, T.D.W. Claridge, M.A. McDonough, C.J. Schofield, Nat. Chem. 6, 1084–1090 (2014)

    Article  CAS  Google Scholar 

  20. N. Hotta, Y. Akanuma, R. Kawamori, K. Matsuoka, Y. Oka, M. Shichiri, T. Toyota, M. Nakashima, I. Yoshimura, N. Sakamoto, Y. Shigeta, Diabetes Care 29, 1538–1544 (2006)

    Article  CAS  Google Scholar 

  21. A. Degterev, A. Lugovskoy, M. Cardone, B. Mulley, G. Wagner, T. Mitchison, J. Yuan, Nat. Cell Biol. 3, 173–182 (2001)

    Article  CAS  Google Scholar 

  22. R. Dayam, T. Sanchez, O. Clement, R. Shoemaker, S. Sei, N. Neamati, J. Med. Chem. 48, 111–120 (2005)

    Article  CAS  Google Scholar 

  23. S. Kobayashi, H. Ishitani, Chem. Rev. 99, 1069–1094 (1999)

    Article  CAS  Google Scholar 

  24. C. Palomo, J.M. Aizpurua, I. Ganboa, M. Oiarbide, Eur. J. Org. Chem. 1999, 3223–3235 (1999)

  25. P. Buonora, J.-C. Olsen, T. Oh, Tetrahedron 57, 6099–6138 (2001)

    Article  CAS  Google Scholar 

  26. G.K. Friestad, A.K. Mathies, Tetrahedron 63, 2541–2569 (2007)

    Article  CAS  Google Scholar 

  27. V.V. Kouznetsov, Tetrahedron 65, 2721–2750 (2009)

    Article  CAS  Google Scholar 

  28. M. Terada, Synthesis 2010, 1929–1982 (2010)

  29. T.C. Nugent, M. El-Shazly, Adv. Synth. Catal. 352, 753–819 (2010)

    Article  CAS  Google Scholar 

  30. J. Wang, X. Liu, X. Feng, Chem. Rev. 111, 6947–6983 (2011)

    Article  CAS  Google Scholar 

  31. S. Kobayashi, Y. Mori, J.S. Fossey, M.M. Salter, Chem. Rev. 111, 2626–2704 (2011)

    Article  CAS  Google Scholar 

  32. P.H.-Y. Cheong, C.Y. Legault, J.M. Um, N. Celebi-Ölcüm, K.N. Houk, Chem. Rev. 111, 5042–5137 (2011)

    Article  CAS  Google Scholar 

  33. D. Parmar, E. Sugiono, S. Raja, M. Rueping, Chem. Rev. 114, 9047–9153 (2014)

    Article  CAS  Google Scholar 

  34. G. Blay, R.M. Giron, M. Montesinos-Magraner, J.R. Pedro, Eur. J. Org. Chem. 2013, 3885–3895 (2013)

  35. N. George, M. Bekkaye, A. Alix, J. Zhu, G. Masson, Chem. Eur. J. 20, 3621–3625 (2014)

    Article  CAS  Google Scholar 

  36. T. Kano, T. Yurino, D. Asakawa, K. Maruoka, Angew. Chem. Int. Ed. 52, 5532–5534 (2013)

    Article  CAS  Google Scholar 

  37. T. Kano, T. Yurino, K. Maruoka, Angew. Chem. Int. Ed. 52, 11509–11512 (2013)

    Article  CAS  Google Scholar 

  38. B. Ranieri, A. Sartori, C. Curti, L. Battistini, G. Rassu, G. Pelosi, G. Casiraghi, F. Zanardi, Org. Lett. 16, 932–935 (2014)

    Article  CAS  Google Scholar 

  39. T. Kano, R. Kobayashi, K. Maruoka, Angew. Chem. Int. Ed. 54, 8471–8474 (2015)

    Article  CAS  Google Scholar 

  40. T. Kano, Y. Aota, D. Asakawa, K. Maruoka, Chem. Commun. 51, 16472–16474 (2015)

    Article  CAS  Google Scholar 

  41. T. Yurino, Y. Aota, D. Asakawa, T. Kano, K. Maruoka, Tetrahedron 72, 3687–3700 (2016)

    Article  CAS  Google Scholar 

  42. K. Zou, J. Ye, X.-Y. Wu, Tetrahedron 71, 7869–7873 (2015)

    Article  CAS  Google Scholar 

  43. Y. Liang, E.B. Rowland, G.B. Rowland, J.A. Perman, J.C. Antilla, Chem. Commun. 46, 4477–4479 (2007)

  44. S. Fu, H. Jiang, Y. Deng, W. Zeng, Adv. Synth. Catal. 353, 2795–2804 (2011)

    Article  CAS  Google Scholar 

  45. S. Maitia, P. Mal, Adv. Synth. Catal. 357, 1416–1424 (2015)

    Article  Google Scholar 

  46. L.D.S. Yadav, B.S. Yadav, V.K.J. Rai, J. Heterocycl. Chem. 45, 1315–1319 (2008)

    Article  CAS  Google Scholar 

  47. F. Yu, H. Hu, X. Gu, J. Ye, Org. Lett. 14, 2038–2041 (2012)

    Article  CAS  Google Scholar 

  48. W. Wu, H. Huang, X. Yuan, K. Zhu, J. Ye, Chem. Commun. 48, 9180–9182 (2012)

    Article  CAS  Google Scholar 

  49. K. Zhu, H. Huang, W. Wu, Y. Wei, J. Ye, Chem. Commun. 49, 2157–2159 (2013)

    Article  CAS  Google Scholar 

  50. H. Zhang, B. Wang, L. Cui, Y. Li, J. Qu, Y. Song, Org. Biomol. Chem. 12, 9097–9100 (2014)

    Article  CAS  Google Scholar 

  51. A. Hvala, L.J. Soršak, G. Soršak, U. Bratušek, J. Svete, N. Lah, I. Leban, B. Stanovnik, Heterocycles 57, 791–809 (2002)

    Article  CAS  Google Scholar 

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Acknowledgements

This work was partially supported by the National Natural Science Foundation of China (21272068, 21572056), Program for New Century Excellent Talents in University (NCET-13-0800), and the Fundamental Research Funds for the Central Universities.

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Authors and Affiliations

  1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237, People’s Republic of China

    Kaihe Zou & Xin-Yan Wu

  2. Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, People’s Republic of China

    Jinxing Ye

  3. Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, People’s Republic of China

    Jinxing Ye

Authors
  1. Kaihe Zou
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  2. Xin-Yan Wu
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Correspondence to Xin-Yan Wu or Jinxing Ye.

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Zou, K., Wu, XY. & Ye, J. Brønsted acid-catalyzed aza-Mannich reaction of N-Boc aminals: access to multifunctional rhodanine/hydantoin derivatives. Res Chem Intermed 43, 4503–4516 (2017). https://doi.org/10.1007/s11164-017-2892-9

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