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Imidazole as an efficient catalyst for the synthesis of 2-amino-3-cyano-4H-chromen-4yl-phosphonates

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Abstract

An efficient procedure for the preparation of 2-amino-3-cyano-4H-chromen-4-yl phosphonate derivatives via a three-component reaction of salicylaldehyde, malononitrile and trialkyl phosphites or diethyl phosphite using inexpensive and environmentally friendly imidazole as organocatalyst has been reported. Beside excellent yields and easy workup, the reaction is done in an almost neutral medium.

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References

  1. L.D. Quin, A Guide to Organophosphorus Chemistry (Wiley, New York, 2001), pp. 351–378

    Google Scholar 

  2. W.M. Abdou, A.A. Shaddy, ARKIVOC 9, 143 (2009)

    Google Scholar 

  3. P.H. Clézardin, F.H. Ebetino, P.G.J. Fournier, Cancer Res. 65, 4971 (2005)

    Article  Google Scholar 

  4. A.M. Downey, C.W. Cairo, Med. Chem. Commun. 5, 1619 (2014)

    Article  CAS  Google Scholar 

  5. P. Savignac, B. Iorga, Modern Phosphonate Chemistry (CRC Press, Boca Raton, 2003)

    Book  Google Scholar 

  6. S.J. Mohr, M.A. Chirigos, F.S. Fuhrman, J.W. Pryor, Cancer Res. 35, 3750 (1975)

    CAS  Google Scholar 

  7. P.W. Smith, S.L. Sollis, P.D. Howes, P.C. Cherry, I.D. Starkey, K.N. Cobley, H. Weston, J. Scicinski, A. Merritt, A. Whittington, P. Wyatt, N. Taylor, D. Green, R. Bethell, S. Madar, R.J. Fenton, P.J. Morley, T. Pateman, A. Beresford, J. Med. Chem. 41, 787 (1998)

    Article  CAS  Google Scholar 

  8. M.M. Khafagy, A.H.F. Abd El-Wahab, F.A. Eid, A.M. El-Agrody, IL Farmaco 57, 715 (2002)

    Article  CAS  Google Scholar 

  9. D.R. Anderson, Sh Hegde, E. Reinhard, L. Gomez, W.F. Vernier, L. Lee, Sh Liu, A. Sambandam, P.A. Snider, L. Masih, Bioorg Med. Chem. Lett. 15, 1587 (2005)

    Article  CAS  Google Scholar 

  10. A.A. Jensen, M.N. Erichsen, C.W. Nielsen, T.B. Stensbøl, J. Kehler, L. Bunch, J. Med. Chem. 52, 912 (2009)

    Article  CAS  Google Scholar 

  11. Y. He, R. Hu, R. Tong, F. Li, J. Shi, M. Zhang, Molecules 19, 19253 (2014)

    Article  Google Scholar 

  12. M. Rajasekhar, K.U.M. Rao, C.S. Sundar, N.M.B. Reddy, S.K. Nayak, C.S. Reddy, Chem. Pharm. Bull. 60, 845 (2012)

    Article  Google Scholar 

  13. R.M.N. Kalla, J.-S. Choi, J.-W. Yoo, S.J. Byeon, M.S. Heo, I. Kim, Eur. J. Med. Chem. 76, 61 (2014)

    Article  CAS  Google Scholar 

  14. P. Jayashree, G. Shanthi, P.T. Perumal, Synlett 06, 917 (2009)

    Google Scholar 

  15. B. Das, P. Balasubramanyam, G.C. Reddy, N. Salvanna, Helv. Chim. Acta 94, 1347 (2011)

    Article  CAS  Google Scholar 

  16. M.A. Kulkarni, V.R. Pandurangi, U.V. Desai, P.P. Wadgaonkar, C. R. Chimie 15, 745 (2012)

    Article  CAS  Google Scholar 

  17. S.R. Kolla, Y.R. Lee, Tetrahedron 68, 226 (2012)

    Article  CAS  Google Scholar 

  18. S. Sobhani, M. Honarmand, Catal. Lett. 143, 476 (2013)

    Article  CAS  Google Scholar 

  19. M.A. Kulkarni, U.P. Lad, U.V. Desai, S.D. Mitragotri, P.P. Wadgaonkar, C. R. Chimie 16, 148 (2013)

    Article  CAS  Google Scholar 

  20. R. Mohammadi, M.Z. Kassaee, J. Mol. Catal. A Chem. 380, 152 (2013)

    Article  CAS  Google Scholar 

  21. R.M.N. Kalla, S.J. Byeon, M.S. Heo, I. Kim, Tetrahedron 69, 10544 (2013)

    Article  CAS  Google Scholar 

  22. P. Dai, G. Zha, X. Lai, W. Lie, Q. Gan, Y. Shen, RSC Adv. 4, 63420 (2014)

    Article  CAS  Google Scholar 

  23. M. R. Grimmett, in Comprehensive Heterocyclic Chemistry II, Vol. 3A, ed. By R. Katritsky, E. F. V. Scriven (Pergamon: Oxford, 1996), P. 77

  24. S.K. Verma, B.N. Acharya, M.P. Kaushik, Org. Lett. 12, 4232 (2010)

    Article  CAS  Google Scholar 

  25. X.-G. Huang, J. Liu, J. Ren, T. Wang, W. Chen, B.-B. Zeng, Tetrahedron 67, 6202 (2011)

    Article  CAS  Google Scholar 

  26. X.-G. Huang, M. Shi, Org. Biomol. Chem. 30, 2343 (2012)

    Google Scholar 

  27. M. NasimKhan, S. Pal, S. Karamthullah, L.H. Choudhury, RSC Advances 4, 3732 (2014)

    Article  Google Scholar 

  28. Y. Okamoto, Y. Kaneda, T. Yamasaki, T. Okawara, M. Furukawa, J. Chem. Soc. Perkin Trans. 1, 1323 (1997)

    Article  Google Scholar 

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Correspondence to Fatemeh Darvish.

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Darvish, F., Abdollahzade, A. & Saravani, D. Imidazole as an efficient catalyst for the synthesis of 2-amino-3-cyano-4H-chromen-4yl-phosphonates. Res Chem Intermed 43, 1487–1494 (2017). https://doi.org/10.1007/s11164-016-2710-9

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