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Click and facile access of substituted tetrahydro-4H-chromenes using 2-aminopyridine as a catalyst

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Abstract

A highly convenient and greener method for the facile synthesis of pharmaceutically diverse 2-amino-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles via a one-pot, three component condensation of aromatic aldehydes, malononitrile, and 1,3-cyclohexanedione or dimedone using 2-aminopyridine as an efficient alkaline organo catalyst is described. This new chemistry furnishes the desired heterocycles in very shorter reaction times with higher purity and has the advantages of economic viability, ease of preparation, excellent yields, and recyclability of catalyst.

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References

  1. S.L. Schreiber, Science 287, 1964 (2000)

    Article  CAS  Google Scholar 

  2. L.F. Tietze, Chem. Rev. 96, 115 (1996)

    Article  CAS  Google Scholar 

  3. B.M. Trost, Angew. Chem. Int. Ed. 34, 259 (1995)

    Article  CAS  Google Scholar 

  4. G.J. Kelly, F. King, M. Kett, Green Chem. 4, 392 (2002)

    Article  CAS  Google Scholar 

  5. J. Weitkamp, M. Hunger, U. Rymsa, Microporous Mesoporous Mater. 48, 255 (2001)

    Article  CAS  Google Scholar 

  6. R.A. Sheldon, Pure Appl. Chem. 72, 1233 (2000)

    Article  CAS  Google Scholar 

  7. A. Zapf, M. Beller, Top. Catal. 19, 101 (2002)

    Article  CAS  Google Scholar 

  8. S. Bertelsen, K.A. Jorgensen, Chem. Soc. Rev. 38, 2178 (2009)

    Article  CAS  Google Scholar 

  9. F. Giacalone, M. Gruttadauria, P. Agrigento, R. Noto, Chem. Soc. Rev. 41, 2406 (2012)

    Article  CAS  Google Scholar 

  10. M.J. Gaunt, C.C. Johansson, A. McNally, N.T. Vo, Drug Discov. Today 12, 8 (2007)

    Article  CAS  Google Scholar 

  11. P.A. Tempest, Curr. Opin. Drug Discov. 8, 776 (2005)

    CAS  Google Scholar 

  12. H. Fujioka, K. Murai, O. Kubo, Y. Ohba, Y. Kita, Org. Lett. 9, 1687 (2007)

    Article  CAS  Google Scholar 

  13. N.M. Evdokimov, A.S. Kireev, A.A. Yakovenko, M.Y. Antipin, I.V. Magedov, A. Kornienko, J. Org. Chem. 72, 3443 (2007)

    Article  CAS  Google Scholar 

  14. X.S. Wang, Q. Li, J.R. Wu, Y.L. Li, C.S. Yao, S.J. Tu, Synthesis 12, 1902 (2008)

  15. P.A. Wender, S.T. Handy, D.L. Wright, Chem. Ind. 19, 765 (1997)

  16. X. Li, Y. Zhao, H. Qu, Z. Mao, X. Lin, Chem. Commun. 49, 1401 (2013)

    Article  CAS  Google Scholar 

  17. N. Erdmann, A.R. Philipps, I. Atodiresei, D. Enders, Adv. Synth. Catal. 355, 847 (2013)

    Article  CAS  Google Scholar 

  18. F. Shi, W. Tan, R.Y. Zhu, G.J. Xing, S.J. Tu, Adv. Synth. Catal. 355, 1605 (2013)

    Article  CAS  Google Scholar 

  19. X. Meng, C. Yu, P. Zhao, RSC Adv. 4, 8612 (2014)

    Article  CAS  Google Scholar 

  20. X. Meng, Y. Wang, C. Yu, P. Zhao, RSC Adv. 4, 27301 (2014)

    Article  CAS  Google Scholar 

  21. J. Skommer, D. Wlodkowic, M. Matto, M. Eray, J. Pelkonen, Leuk. Res. 30, 322 (2006)

    Article  CAS  Google Scholar 

  22. W. Kemnitzer, S. Kasibhatla, S. Jiang, H. Zhang, J. Zhao, S. Jia, L. Xu, G.C. Grundy, R. Denis, N. Barriault, L. Vaillancourt, S. Charron, J. Dodd, G. Attardo, D. Labrecque, S. Lamothe, H. Gourdeau, B. Tseng, J. Drewe, S.X. Cai, Bioorg. Med. Chem. Lett. 15, 4745 (2005)

    Article  CAS  Google Scholar 

  23. H. Gourdeau, L. Leblond, B. Hamelin, C. Desputeau, K. Dong, S. Kianicka, B. Tseng, Mol. Cancer Ther. 3, 1375 (2004)

    CAS  Google Scholar 

  24. G.A. Reynolds, K.H. Drexhage, Opt. Commun. 13, 222 (1975)

    Article  CAS  Google Scholar 

  25. H. Zollinger, Color Chemistry, 3rd edn. (Verlag Helvetica Chimica Acta and Wiley, Zurikh and Weinheim, 2003)

    Google Scholar 

  26. E.R. Bissell, A.R. Mitchell, R. Smith, Eur. J. Org. Chem. 45, 2283 (1980)

    Article  CAS  Google Scholar 

  27. G.P. Ellis, Chemistry of heterocyclic of compounds, in A. Weissberger, E.C. Taylor, (John Wiley, New York, 1977)

  28. E.A. Hafez, M.H. Elnagdi, A.G. Elagamey, F.M.A. Taweel, Heterocycles 26, 903 (1987)

    Article  CAS  Google Scholar 

  29. M.G. Dekamin, M. Eslami, A. Maleki, Tetrahedron 69, 1074 (2013)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  31. A. Hasaninejad, M. Shekouhy, N. Golzar, A. Zare, M.M. Doroodmand, Appl. Catal. A 402, 11 (2011)

    Article  CAS  Google Scholar 

  32. V.M. Joshi, R.L. Magar, P.M. Throat, S.U. Tekale, B.R. Patil, M.P. Kale, R.P. Pawar, Chin. Chem. Lett. 25, 455 (2014)

    Article  CAS  Google Scholar 

  33. S. Khaksar, A. Rouhollahpour, S.M. Talesh, J. Fluor. Chem. 141, 11 (2012)

    Article  CAS  Google Scholar 

  34. A. Hasaninejad, N. Golzar, M. Beyrati, A. Zare, M.M. Doroodmand, J. Mol. Catal. A Chem. 372, 137 (2013)

    Article  CAS  Google Scholar 

  35. K. Niknam, N. Borazjani, R. Rashidian, A. Jamali, Chin. J. Catal. 34, 2245 (2013)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  37. S.M. Baghbanian, N. Rezaei, H. Tashakkorian, Green Chem. 15, 3446 (2013)

    Article  CAS  Google Scholar 

  38. M. Gupta, V.K. Gupta, New J. Chem. 39, 3578 (2015)

    Article  CAS  Google Scholar 

  39. A.F. Shojaei, K. Tabatabaeian, F. Shirini, S.Z. Hejazi, RSC Adv. 4, 9509 (2014)

    Article  Google Scholar 

  40. O.H. Qareaghaja, S. Mashkouria, M.R.N. Jamala, G. Kaupp, RSC Adv. 4, 48191 (2014)

    Article  Google Scholar 

  41. A.T. Khan, M. Lal, S. Ali, M. Musawwer, Khan. Tetrahedron Lett. 52, 5327 (2011)

    Article  CAS  Google Scholar 

  42. I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45, 8625 (2004)

    Article  CAS  Google Scholar 

  43. R. Ramesh, A. Lalitha, RSC Adv. 5, 51188 (2015)

    Article  CAS  Google Scholar 

  44. R. Ramesh, S. Maheswari, S. Murugesan, R. Sandhiya, A. Lalitha, Res. Chem. Intermed. 41, 8233 (2015)

    Article  CAS  Google Scholar 

  45. R. Ramesh, A. Lalitha, Res. Chem. Intermed. 41, 8009 (2015)

    Article  CAS  Google Scholar 

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Acknowledgments

R. R. gratefully acknowledge the DST-Inspire Fellowship, New Delhi, India (No: DST/INSPIRE Fellowship/2012/690) for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Periyar University, Periyar Palkalai Nagar, Salem, Tamil Nadu, 636011, India

    Rathinam Ramesh, Subramani Maheswari & Appaswami Lalitha

  2. Department of Chemistry, Salem Sowdeswari College, Salem, Tamil Nadu, 636010, India

    Pullar Vadivel

Authors
  1. Rathinam Ramesh
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  2. Pullar Vadivel
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  3. Subramani Maheswari
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  4. Appaswami Lalitha
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Correspondence to Appaswami Lalitha.

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Ramesh, R., Vadivel, P., Maheswari, S. et al. Click and facile access of substituted tetrahydro-4H-chromenes using 2-aminopyridine as a catalyst. Res Chem Intermed 42, 7625–7636 (2016). https://doi.org/10.1007/s11164-016-2557-0

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  • DOI: https://doi.org/10.1007/s11164-016-2557-0

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