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Cheap thiamine hydrochloride as efficient catalyst for synthesis of 4H-benzo[b]pyrans in aqueous ethanol

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Abstract

Preparation of pharmaceutically active 2-amino-4H-pyran derivatives has been achieved using cheap thiamine hydrochloride as catalyst. A wide range of aromatic aldehydes easily undergo condensation with malononitrile and several kinds of 1,3-cyclohexanedione under mild condition to afford the desired product with good purity in excellent yield. This protocol has various advantages as a simple, clean, and environmentally benign three-component process.

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References

  1. J.E.G. Kemp, in Comprehensive Organic Synthesis, ed. by B.M. Trost, I. Fleming (Pergamon, Oxford, 1991), p. 469

    Chapter  Google Scholar 

  2. A. Domling, Chem. Rev. 106, 17 (2014)

    Article  Google Scholar 

  3. B.B. Toure, D.G. Hall, Chem. Rev. 109, 4439 (2009)

    Article  CAS  Google Scholar 

  4. D. Kumar, V.B. Reddy, S. Sharad, U. Dube, S. Kapur, Eur. J. Med. Chem. 44, 3805 (2009)

    Article  CAS  Google Scholar 

  5. Y.M. Litvinov, A.M. Shestopalov, in Advances in Heterocyclic Chemistry, vol. 103, ed. by A.R. Katritzky (Academic Press, New York, 2011), p. 175

  6. I.A. Azath, P. Puthiaraj, K. Pitchumani, ACS Sustain. Chem. Eng. 1, 174 (2016)

    Google Scholar 

  7. R.Y. Guo, Z.M. An, L.P. Mo, R.Z. Wang, H.X. Liu, S.X. Wan, Z.H. Zhang, ACS Comb. Sci. 15, 557 (2013)

    Article  CAS  Google Scholar 

  8. K. Aswin, S.S. Mansoor, K. Logaiya, S.P.N. Sudhan, V.S. Malik, H. Ramadoss, Res. Chem. Intermed. 40, 2583 (2014)

    Article  CAS  Google Scholar 

  9. H.R. Safaei, M. Shekouhy, S. Rahmanpur, S. Athar, Green Chem. 14, 1696 (2012)

    Article  CAS  Google Scholar 

  10. M.M. Heravi, Y.S. Beheshtiha, Z. Pirnia, S. Sadjadi, M. Adibi, Synth. Commun. 39, 3663 (2009)

    Article  CAS  Google Scholar 

  11. D.M. Pore, K.A. Undale, B.B. Dongare, U.V. Desai, Catal. Lett. 132, 104 (2009)

    Article  CAS  Google Scholar 

  12. L.M. Wang, J.H. Shao, H. Tian, Y.H. Wang, B. Liu, J. Fluor. Chem. 127, 97 (2006)

    Article  CAS  Google Scholar 

  13. S. Balalaie, M. Sheikh-Ahmadi, M. Bararjanian, Catal. Commun. 8, 1724 (2007)

    Article  CAS  Google Scholar 

  14. R. Hekmatshoar, S. Majedi, K. Bakhtiari, Catal. Commun. 9, 307 (2008)

    Article  CAS  Google Scholar 

  15. W.B. Sun, P. Zhang, J. Fan, S.H. Chen, Z.H. Zhang, Synth. Commun. 40, 587 (2010)

    Article  CAS  Google Scholar 

  16. S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, P. Salehi, Synth. Commun. 37, 1097 (2007)

    Article  CAS  Google Scholar 

  17. Y. Peng, G. Song, F. Huang, Monatsh. Chem. 136, 727 (2005)

    Article  CAS  Google Scholar 

  18. L. Chen, Y.Q. Li, X.J. Huang, W.J. Zheng, Heteroat. Chem. 20, 91 (2009)

    Article  CAS  Google Scholar 

  19. P. Dünkelmann, D.K. Jung, A. Nitsche, A.S. Demir, P. Siegert, B. Lingen, M. Baumann, M. Pohl, M. Müller, J. Am. Chem. Soc. 124, 12084 (2002)

    Article  Google Scholar 

  20. S. Orlandi, M. Caporale, M. Benaglia, R. Annunziata, Tetrahedron Asymmetry 14, 3827 (2003)

    Article  CAS  Google Scholar 

  21. C. Noonan, L. Baragwanath, S.J. Connon, Tetrahedron Lett. 49, 4003 (2008)

    Article  CAS  Google Scholar 

  22. S. Goswami, A. Hazra, Chem. Lett. 38, 484 (2009)

    Article  CAS  Google Scholar 

  23. M. Lei, L. Ma, L. Hu, Tetrahedron Lett. 50, 6393 (2009)

    Article  CAS  Google Scholar 

  24. P.G. Mandhane, P.S. Joshi, D.R. Nagargoje, C.H. Gill, Tetrahedron Lett. 51, 3138 (2010)

    Article  CAS  Google Scholar 

  25. Y. Gao, D.M. Du, Tetrahedron Asymmetry 23, 1343 (2012)

    Article  CAS  Google Scholar 

  26. S.M. Baghbanian, N. Rezaeia, H. Tashakkorianb, Green Chem. 15, 3446 (2013)

    Article  CAS  Google Scholar 

  27. M.A. Nasseri, S.M. Sadeghzadeh, Monatsh. Chem. 144, 1551 (2013)

    Article  CAS  Google Scholar 

  28. M. Abedini, F. Shirini, J.M.A. Omran, M. Seddighi, O. Goli-Jolodar, Res. Chem. Intermed. 42, 4443 (2016)

    Article  CAS  Google Scholar 

  29. L. Edjlali, R.H. Khanamiri, Monatsh. Chem. 147, 1221 (2016)

    Article  CAS  Google Scholar 

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Acknowledgements

We thank the National Natural Science Foundation of China (21302146), Scientific Research Foundation for the Returned Oversea as Chinese Scholar, State Education Ministry ([2015]1098), and Science Foundation for Young Teachers of Wuyi University (2015td01).

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Authors and Affiliations

  1. School of Chemical and Environmental Engineering, Wuyi University, Jiangmen, China

    Lu Chen, Sunan Bao, Lixiang Yang, Xian Zhang, Bin Li & Yibiao Li

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  1. Lu Chen
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  2. Sunan Bao
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  3. Lixiang Yang
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  4. Xian Zhang
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  5. Bin Li
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  6. Yibiao Li
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Correspondence to Lu Chen.

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Chen, L., Bao, S., Yang, L. et al. Cheap thiamine hydrochloride as efficient catalyst for synthesis of 4H-benzo[b]pyrans in aqueous ethanol. Res Chem Intermed 43, 3883–3891 (2017). https://doi.org/10.1007/s11164-016-2843-x

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