Advertisement

Journal of the Iranian Chemical Society

, Volume 15, Issue 7, pp 1647–1654 | Cite as

A facile and expedient microwave-assisted solvent-free method for the synthesis of 2-amino-4-(2-oxo-2H-chromen-3-yl)nicotinonitriles

Original Paper

Abstract

An efficient method for the synthesis of novel 2-amino-4-(2-oxo-2H-chromen-3-yl)nicotinonitriles has been developed under solvent-free conditions using enaminonitriles and various aliphatic amines. 3-acetyl-2H-chromen-2-one (1) reacted with malononitirle in ethanol using l-proline as a base to give 2-(1-(2-oxo-2H-chromen-3-yl)ethylidene)malononitrile (2) which on reaction with dimethylformamide dimethyl acetal (DMF-DMA) resulted in the formation of 2-(3-(dimethylamino)-1-(2-oxo-2H-chromen-3-yl)allylidene)malononitrile (3). The later on reaction with various aliphatic amines under solvent-free conditions gave the title compounds, i.e., 2-amino-4-(2-oxo-2H-chromen-3-yl)nicotinonitriles (4). Microwave irradiation method has also been applied successfully to achieve the compounds in excellent yields.

Graphical Abstract

Keywords

Coumarins 2-Amino-3-cyanopyridines Solvent-free method Microwave irradiation 

Notes

Acknowledgements

The authors are thankful to the authorities of Jawaharlal Nehru Technological University Hyderabad for providing laboratory facilities. They are grateful to the Department of Science & Technology, Govt. of India, New Delhi, for the financial support in the form of INSPIRE Fellowship to one of them (D.S.).

Supplementary material

13738_2018_1363_MOESM1_ESM.doc (46.2 mb)
Supplementary material 1 (DOC 47268 kb)

References

  1. 1.
    M. Cacic, M. Trkovnik, F. Cacic, E. Asschon, Molecules 11, 134 (2006)CrossRefGoogle Scholar
  2. 2.
    Y. Kashman, K.R. Gustafson, R. Fuller, J.H. Cardellina, J.B. McMahon, M.J. Currens, R. Buckheit, S.H. Hughes, G.M. Cragg, M.R. Boyd, J. Med. Chem. 35, 2735 (1992)CrossRefGoogle Scholar
  3. 3.
    S.R. Natala, R.M. Muralidhar, C. Stephen, G. Kiranmai, C.B. Stanley, R.E. Premkumar, R.M.V. Ramana, Bioorg. Med. Chem. Lett. 14, 4093 (2004)CrossRefGoogle Scholar
  4. 4.
    Z. Ye, Z. Biqun, C. Zhenfeng, P. Yingming, W. Hengshan, L. Hong, Y. Xianghui, Bioorg. Med. Chem. Lett. 21, 6811 (2011)CrossRefGoogle Scholar
  5. 5.
    R.B. William, D. Alan, C. York, A. Macintosh, J. Guilford, J. Phys. Chem. 94, 5020 (1990)CrossRefGoogle Scholar
  6. 6.
    K.C. Fylaktakidou, D.J. Hadjipavlou-Litina, K.E. Litinas, D.N. Nicolaides, Curr. Pharm. Des. 10, 3813 (2004)CrossRefGoogle Scholar
  7. 7.
    G.D. Henry, Tetrahedron 60, 6043 (2004)CrossRefGoogle Scholar
  8. 8.
    J.P. Michael, Nat. Prod. Rep. 22, 627 (2005)CrossRefGoogle Scholar
  9. 9.
    C. Temple, G.A. Rener, W.R. Waud, P.E. Noker, J. Med. Chem. 35, 3686 (1992)CrossRefGoogle Scholar
  10. 10.
    S. Drabu, S. Singh, S. Munirajam, N. Kumar, Indian J. Heterocycl. Chem. 16, 411 (2007)Google Scholar
  11. 11.
    P. Victory, J. Cirujeda, A.A. Vidal-Ferran, Tetrahedron 51, 10253 (1995)CrossRefGoogle Scholar
  12. 12.
    B.C.H. May, J.A. Zorn, J. Witkop, J. Sherrill, A.C. Wallace, G. Legname, S.B. Prusiner, F.E. Cohen, J. Med. Chem. 50, 65 (2007)CrossRefGoogle Scholar
  13. 13.
    K. Guo, R. Mutter, W. Heal, T.K.R. Reddy, H. Cope, S. Pratt, M.J. Thompson, B. Chen, Eur. J. Med. Chem. 43, 93 (2008)CrossRefGoogle Scholar
  14. 14.
    M.T. Cocco, C. Congiu, V. Lilliua, V. Onnis, Bioorg. Med. Chem. 15, 1859 (2007)CrossRefGoogle Scholar
  15. 15.
    T. Murata, M. Shimada, S. Sakakibara, T. Yoshino, H. Kadono, T. Masuda, M. Shimazaki, T. Shintani, K. Fuchikami, K. Sakai, H. Inbe, K. Takeshita, T. Niki, M. Umeda, K.B. Bacon, K.B. Ziegelbauer, T.B. Lowinger, Bioorg. Med. Chem. Lett. 13, 913 (2003)CrossRefGoogle Scholar
  16. 16.
    M. Mantri, D.O. Graaf, V.J. Van, A. Goblyos, F.D.J.K. Von, T. Mulder-Krieger, R. Link, D.H. Vries, M.W. Beukers, J. Brussee, A.P. Ijzerman, J. Med. Chem. 51, 4449 (2008)CrossRefGoogle Scholar
  17. 17.
    F. Zhang, Y. Zhao, L. Sun, L. Ding, Y. Gu, P. Gong, Eur. J. Med. Chem. 46, 3149 (2011)CrossRefGoogle Scholar
  18. 18.
    S.R. Sarda, J.D. Kale, S.K. Wasmatkar, V.S. Kadam, P.G. Ingole, W.N. Jadhav, R.P. Pawar, Mol. Divers. 13, 545 (2009)CrossRefGoogle Scholar
  19. 19.
    N. Kumar, A. Chauhan, S. Drabu, Biomed. Pharmacother. 65, 375 (2011)CrossRefGoogle Scholar
  20. 20.
    J. Deng, T. Sanchez, L.Q. Al-Mawsawi, R. Dayam, R.A. Yunes, A. Garofalo, M.B. Bolger, N. Neamati, Bioorg. Med. Chem. 15, 4985 (2007)CrossRefGoogle Scholar
  21. 21.
    B.M. Trost, Science 254, 1471 (1991)CrossRefGoogle Scholar
  22. 22.
    A. Corma, H. Garcia, Chem. Rev. 103, 4307 (2003)CrossRefGoogle Scholar
  23. 23.
    F. Toda, Acc. Chem. Res. 28, 480 (1995)CrossRefGoogle Scholar
  24. 24.
    S.J. Ji, Z.L. Shen, D.G. Gu, X.Y. Huang, Ultrason. Sonochem. 12, 161 (2005)CrossRefGoogle Scholar
  25. 25.
    Z.L. Shen, S.J. Ji, T.P. Loh, Tetrahedron Lett. 46, 507 (2005)CrossRefGoogle Scholar
  26. 26.
    A.P. Marcos, C.P. Martins, D.N. Frizzo, L.B. Moreira, M. Pablo, Chem. Rev. 109, 4140 (2009)CrossRefGoogle Scholar
  27. 27.
    L. Amy, O.K. Peter, E.H. Matthew, A.C. Richard, J. Comb. Chem. 4, 95 (2002)CrossRefGoogle Scholar
  28. 28.
    D. Srikrishna, S. Tasqeeruddin, P.K. Dubey, Lett. Org. Chem. 11, 556 (2014)CrossRefGoogle Scholar
  29. 29.
    D. Srikrishna, P.K. Dubey, Tetrahedron Lett. 55, 6561 (2014)CrossRefGoogle Scholar
  30. 30.
    D. Srikrishna, A. Mallika, P.K. Dubey, Indian J. Chem. 56B, 96 (2017)Google Scholar
  31. 31.
    D. Srikrishna, G. Chandraiah, P.K. Dubey, Mini-Rev. Med. Chem. (2016).  https://doi.org/10.2174/1389557516666160801094919 Google Scholar
  32. 32.
    D. Srikrishna, P.K. Dubey, New J. Chem. 41, 5168 (2017)CrossRefGoogle Scholar
  33. 33.
    G.H. Tamam, H.M. Bakeer, R.M. Abdel, W.A. Arafa, J. Chin. Chem. Soc. 52, 1191 (2005)CrossRefGoogle Scholar
  34. 34.
    M.A. Zaharan, E.B. Pedersen, C. Nielsen, Monatsh. Chem. 126, 1271 (1995)CrossRefGoogle Scholar
  35. 35.
    L.B. Kayleigh, S. Jennifer, C.C. Waby, S. Graham, Tetrahedron Lett. 58, 1467 (2017)CrossRefGoogle Scholar
  36. 36.
    L. Eugene, S.C. Tai, C.N.R. Ramachandra, Org. Synth. Coll. 37, 26 (1957)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  1. 1.Department of ChemistryJawaharlal Nehru Technological University Hyderabad College of EngineeringKukatpally, HyderabadIndia

Personalised recommendations