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Vol. 31 No. 11 (2019): Vol 31 Issue 11

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Catalyst-Free Cascade Synthesis of Densely Functionalized Chromenes in Water

https://doi.org/10.14233/ajchem.2019.22191
Subrahmanya Ishwar Bhat
Department of Chemistry, N.M.A.M. Institute of Technology, Nitte, Karkala-574110, India
https://orcid.org/0000-0001-9528-6176

Corresponding Author(s) : Subrahmanya Ishwar Bhat

subrahmanya@nitte.edu.in

Asian Journal of Chemistry, Vol. 31 No. 11 (2019): Vol 31 Issue 11

Abstract

An expeditious and environmental friendly, general protocol has been developed for the synthesis of 2-amino-3-cyano-4H-chromenes via cascade Knoevenagel-Michael-intramolecular cyclization in water. Pure solid products were obtained by simple filtration technique. The aqueous catalyst-free reactions lead to high product yield at room temperature.

Keywords

Green Synthesis Cascade reaction Water media Knoevenagel condensation Chromenes
Bhat, S. I. (2019). Catalyst-Free Cascade Synthesis of Densely Functionalized Chromenes in Water. Asian Journal of Chemistry, 31(11), 2532–2536. https://doi.org/10.14233/ajchem.2019.22191
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References
  1. P.T. Ananstas and J.C. Warner, Green Chemistry: Theory and Practice, Oxford University Press: New York (1998).
  2. C.J. Li and T.H. Chan, Organic Reactions in Aqueous Media, John Wiley & Sons: New York (1997).
  3. C.I. Herrerias, X. Yao, Z. Li and C.J. Li, Chem. Rev., 107, 2546 (2007); https://doi.org/10.1021/cr050980b.
  4. V.K. Rai, P.K. Rai, S. Bajaj and A. Kumar, Green Chem., 13, 1217 (2011); https://doi.org/10.1039/c0gc00899k.
  5. S. Paul, P. Bhattacharyya and A.R. Das, Tetrahedron Lett., 52, 4636 (2011); https://doi.org/10.1016/j.tetlet.2011.06.101.
  6. M.B. Gawande and P.S. Branco, Green Chem., 13, 3355 (2011); https://doi.org/10.1039/c1gc15868f.
  7. K.C. Nicolaou and J.S. Chen, Chem. Soc. Rev., 38, 2993 (2009); https://doi.org/10.1039/b903290h.
  8. L.Q. Lu, J.R. Chen and W.J. Xiao, Acc. Chem. Res., 45, 1278 (2012); https://doi.org/10.1021/ar200338s.
  9. D.B. Ramachary and M. Kishor, J. Org. Chem., 72, 5056 (2007); https://doi.org/10.1021/jo070277i.
  10. R. Pratap and V.G. Ram, Chem. Rev., 114, 10476 (2014); https://doi.org/10.1021/cr500075s.
  11. M. Curini, G. Cravotto, F. Epifano and G. Giannone, Curr. Med. Chem.,13, 199 (2006);https://doi.org/10.2174/092986706775197890.
  12. R. Ranjith Kumar, S. Perumal, J.C. Menéndez, P. Yogeeswari and D.Sriram, Bioorg. Med. Chem., 19, 3444 (2011); https://doi.org/10.1016/j.bmc.2011.04.033.
  13. G. Brahmachari and B. Banerjee, ACS Sustain. Chem. Eng., 2, 411 (2014); https://doi.org/10.1021/sc400312n.
  14. S. Behravesh, R. Fareghi-Alamdari and R. Badri, Polycycl. Aromat. Compd., 38, 51 (2018); https://doi.org/10.1080/10406638.2016.1149080.
  15. R. Heydari, R. Shahraki, M. Hossaini and A. Mansouri, Res. Chem. Intermed., 43, 4611 (2017); https://doi.org/10.1007/s11164-017-2900-0.
  16. N. Ramireddy, S. Abbaraju, D. Ding, H. Arman and J.C.G. Zhao, J.Heterocycl. Chem., 54, 677 (2017); https://doi.org/10.1002/jhet.2641.
  17. Y. Ren, W. Zhang, J. Lu, K. Gao, X. Liao and X. Chen, RSC Adv., 5, 79405 (2015); https://doi.org/10.1039/C5RA14385C.
  18. M. Gupta, M. Gupta, R. Rajnikant and V.K. Gupta, New J. Chem., 39, 3578 (2015); https://doi.org/10.1039/C4NJ02391A.
  19. M. Fujiwara, M. Sakamoto, K. Komeyama, H. Yoshida and K. Takaki, J. Heterocycl. Chem., 52, 59 (2015); https://doi.org/10.1002/jhet.1964.
  20. A.M. El-Agrody, A.A.M. Al-Dies and A.M. Fouda, Eur. J. Chem., 5, 133 (2014); https://doi.org/10.5155/eurjchem.5.1.133-137.923.
  21. F. Yang, Z. Wang, H. Wang, C. Wang and L. Wang, RSC Adv., 5, 57122 (2015); https://doi.org/10.1039/C5RA10565J.
  22. J. Safari and L. Javadian, Ultrason. Sonochem., 22, 341 (2015); https://doi.org/10.1016/j.ultsonch.2014.02.002.
  23. J. Velasco, E. Pérez-Mayoral, V. Calvino-Casilda, A.J. López-Peinado, M.A. Bañares and E. Soriano, J. Phys. Chem. B, 119, 12042 (2015); https://doi.org/10.1021/acs.jpcb.5b06275.
  24. N. Azizi, M. Mariami and M. Edrisi, Dyes Pigments, 100, 215 (2014); https://doi.org/10.1016/j.dyepig.2013.09.007.
  25. M.M. Heravi, T. Hosseinnejad, Z. Faghihi, M. Shiri and M. Vazinfard, J. Iran. Chem. Soc., 14, 823 (2017); https://doi.org/10.1007/s13738-016-1032-6.
  26. R.G. Vaghei, Z.T. Semiromi and R.K. Nami, Braz. Chem. Soc., 22, 905 (2011).
  27. M.L. Deb and P.J. Bhuyan, Tetrahedron Lett., 46, 6453 (2005); https://doi.org/10.1016/j.tetlet.2005.07.111.
  28. K. Kumaravel and G. Vasuki, Green Chem., 11, 1945 (2009); https://doi.org/10.1039/b913838b.
  29. G. Kumaraswamy, N. Raghu and R.S. Kumar, Org. Prep. Proced. Int., 46, 435 (2014); https://doi.org/10.1080/00304948.2014.944403.
  30. S.I. Bhat, A.R. Choudhury and D.R. Trivedi, RSC Adv., 2, 10556 (2012); https://doi.org/10.1039/c2ra21849f.
  31. J.F. Roudier and A. Foucaud, Synthesis, 159 (1984); https://doi.org/10.1055/s-1984-30764.
  32. M. Costa, F. Areias, L. Abrunhosa, A. Venancio and F. Proenca, J. Org.Chem., 73, 1954 (2008); https://doi.org/10.1021/jo702552f.
  33. D. Kumar, V.B. Reddy, S. Sharad, U. Dube and S. Kapur, Eur. J. Med. Chem., 44, 3805 (2009); https://doi.org/10.1016/j.ejmech.2009.04.017.
  34. B. Robabeh and S.A.N. Shariati, J. Chil. Chem. Soc., 60, 2900 (2015); https://doi.org/10.4067/S0717-97072015000200008.
  35. H. Hu, F. Qiu, A. Ying, J. Yang and H. Meng, Int. J. Mol. Sci., 15, 6897 (2014); https://doi.org/10.3390/ijms15046897.
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