An efficient and facile regioselective synthesis of new substituted (E)-1-(3-aryl-7,8-dihydrocinnoline-5(6H)-ylidene)hydrazines and (1E,2E)-1,2-bis(3-aryl-7,8-dihydrocinnoline-5(6H)-ylidene)hydrazines

Abstract

A study concerning the new substituted cinnoline synthesis is described. The use of a one-pot three-component method allows a simple regioselective and efficient synthesis of cinnoline derivatives via reaction of arylglyoxals with 1,3-cyclohexanedione and dimedone in the presence of hydrazine hydrate.

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References

  1. 1.

    G. Cignarella, D. Barlocco, G.A. Pinna, M.M. Curzu, Acta Chim. Slov. 41, 173 (1994)

    CAS  Google Scholar 

  2. 2.

    G. Cignarella, D. Barlocco, G.A. Pinna, M. Loriga, M.M. Curzu, O. Tofanetti, M. Germini, P. Cazzulani, E. Cavaletti, J. Med. Chem. 32, 2277 (1989)

    CAS  Article  Google Scholar 

  3. 3.

    J.W. Lown, A.R. Morgan, S.F. Yen, Y.H. Wang, W.D. Wilson, Biochemistry 24, 4028 (1990)

    Article  Google Scholar 

  4. 4.

    K. Miyamoto, J. Matsumoto, S. Nakamura, Chem. Abstr. 113, 97619 (1990)

    Google Scholar 

  5. 5.

    A.G. Siegfried, Fr. 1,393,596 (1965)

  6. 6.

    S.M. Yarnal, V.V. Badiger, J. Matsumoto, Chem. Abstr. 104, 224864 (1986)

    Google Scholar 

  7. 7.

    P. Barraja, P. Diana, A. Lauria, A. Passannanti, A.N. Almerico, C. Minnei, S. Longu, D. Cengiu, C. Musiu, P.L. Colla, Bioorg. Med. Chem. 7, 1591 (1999)

    CAS  Article  Google Scholar 

  8. 8.

    G. Cirrincione, E. Almerico, P. Barraja, F. Mingoia, Farmaco 50, 849 (1995)

    CAS  Google Scholar 

  9. 9.

    J. Savaranan, K.S. Manjunath, Indian J. Pharm. Sci. 60, 330 (1998)

    Google Scholar 

  10. 10.

    M.S. Abbady, S.M. Radwan, E.A. Bakhite, Indian J. Chem. Sec B 32, 1281 (1993)

    Google Scholar 

  11. 11.

    E. Gavini, C. Juliano, A. Mule, G. Pirisino, G. Murineddu, G.A. Pinna, Arch Pharm (Weinheim) 333, 341 (2000)

    CAS  Article  Google Scholar 

  12. 12.

    V. Saxena, S.K. Maiti, N. Kumar, A.K. Sharma, Indian J. Anim. Sci. 78, 1250 (2008)

    Google Scholar 

  13. 13.

    S. Vikas, S. Darbhamulla, Afr. Health Sci. 9, 275 (2009)

    Google Scholar 

  14. 14.

    F. Vargas, T. Zoltan, C. Rivas, A. Ramirez, T. Cordero, Y. Díaz, C. Izzo, Y.M. Cárdenas, V. López, L. Gómez, J. Ortega, A. Fuentes, J. Photochem. Photobiol. B: Biol. 92, 83 (2008)

    CAS  Article  Google Scholar 

  15. 15.

    C. Lunniss, C. Eldred, N. Aston, A. Craven, K. Gohil, B. Judkins, S. Keeling, L. Ranshaw, E. Robinson, T. Shipley, N. Trivedi, Bioorg. Med. Chem. Lett. 20, 137 (2010)

    CAS  Article  Google Scholar 

  16. 16.

    R.A. Conrad, W.A. White, US 4,379,929 (1983)

  17. 17.

    Y. Yu, S.K. Singh, A. Liu, T.-K. Li, L.F. Liu, E. LaVoie, J. Bioorg. Med. Chem. 11, 1475 (2003)

    CAS  Article  Google Scholar 

  18. 18.

    T. Nakao, M. Takai, H. Fukamachi, H. Ohashi, Jpn. Kokai Tokkyo Koho JP 11 189,586 [99189,586]

  19. 19.

    E. Lunt, K. Washbourn, W.R. Wragg, J. Chem. Soc. C. 1152 (1968)

  20. 20.

    Hennequin, Laurent Francois Andre. PCT Int. Appl. WO 02 12,228

  21. 21.

    N. Garcia-Dominguez, E. Ravina, L. Santana, C. Teran, G. Garcia-Mera, F. Orallo, M. Crespo, J.A. Fontenla, Arch. Pharma (Weinheim) 321, 735 (1988)

    CAS  Article  Google Scholar 

  22. 22.

    J. Geraint Ger. Offen. 2,438,413 (1975)

  23. 23.

    D. Holland, G. Jones, P.W. Marshall, G.D. Tringham, J. Med. Chem. 19, 1225 (1976)

    CAS  Article  Google Scholar 

  24. 24.

    J.C.E. Simpson, in Condensed Pyridazine and Pyrazine Rings. The Chemistry of Heterocyclic Compounds, ed. by A. Weisberg, (Interscience publishers, New York-London 1953), p. 347

  25. 25.

    G.M. Singerman, in The Chemistry of Heterocyclic Compounds, ed. by R. N. Castle, (Interscience publishers, New York. 1973), p. 1

  26. 26.

    N.J. Leonard, Chem. Rev. 37, 269 (1945)

    CAS  Article  Google Scholar 

  27. 27.

    T.L. Jacobs, in Heterocyclic Compounds, ed. by R. C. Elderfield, (Wiley, New York. 1957) p. 136

  28. 28.

    N. Haider, W. Holzer, “Product Class 9: Cinnolines,” in Science of Synthesis, 2004, pp. 251–313

  29. 29.

    D.J. Brown, Cinnolines and Phthalazines, Suppl. II, The Chemistry of Heterocyclic Compounds (Wiley, New York, 2005)

  30. 30.

    F.M. Abdelrazek, P. Metz, N.H. Metwally, S.F. El-Mahrouky, Arch. Pharm. Chem. Life Sci. (Weinheim) 339, 456 (2006)

    CAS  Article  Google Scholar 

  31. 31.

    B. Wünsch, S. Nerdinger, G. Höfner, Liebigs Ann. 7, 1303 (1995)

    Google Scholar 

  32. 32.

    P.W. Neber, G. Knoller, K. Herrst, A. Trissler, Justus Liebigs Ann. Chem. 471, 113 (1929)

    CAS  Article  Google Scholar 

  33. 33.

    E.J. Alford, K. Schofield, J. Chem. Soc. 2102 (1952)

  34. 34.

    K. Pfannstiel, J. Janecke, Ber. Dtsch. Chem. Ges. 75, 1096 (1942)

    Article  Google Scholar 

  35. 35.

    H.E. Baumgarten, C.H. Anderson, J. Am. Chem. Soc. 80, 1981 (1958)

    CAS  Article  Google Scholar 

  36. 36.

    M.A.M. Gomaa, Tetrahedron Lett. 44, 3493 (2003)

    CAS  Article  Google Scholar 

  37. 37.

    M.S. Shvartsberg, I.D. Ivanchikova, Tetrahedron Lett. 41, 771 (2000)

    CAS  Article  Google Scholar 

  38. 38.

    H.J. Barber, E. Lunt, J. Chem. Soc. C. 1156 (1968)

  39. 39.

    V. Richter, Ber. Dtsch. Chem. Ges. 16, 677 (1883)

    Article  Google Scholar 

  40. 40.

    I.D. Jurberg, F. Gagosz. J. Organomet. Chem. 696, 37 (2011)

    CAS  Article  Google Scholar 

  41. 41.

    G. Halbritter, F. Knoch, H. Kisch, J. Organomet. Chem. 492, 87 (1995)

    CAS  Article  Google Scholar 

  42. 42.

    U. Dürr, F.W. Heinemann, H. Kisch, J. Organomet. Chem. 558, 91 (1998)

    Article  Google Scholar 

  43. 43.

    R.L. Zey, J. Heterocycl. Chem. 25, 847 (1988)

    CAS  Article  Google Scholar 

  44. 44.

    C. Zhu, M. Yamane, Tetrahedron 67, 4933 (2011)

    CAS  Article  Google Scholar 

  45. 45.

    O. Diels, K. Alder, Justus Liebigs Ann. Chem. 450, 237 (1926)

    CAS  Article  Google Scholar 

  46. 46.

    J. Khalafy, M. Rimaz, M. Ezzati, R.H. Prager, Bull. Korean Chem. Soc. 33, 2890 (2012)

    CAS  Article  Google Scholar 

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Acknowledgments

The authors are grateful to Urmia University for financial support and to Dr. A. Choudhury (Missouri University of Science and Technology, USA) for his assistance with X-ray crystallography.

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Correspondence to Jabbar Khalafy.

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Khalafy, J., Ezzati, M., Rimaz, M. et al. An efficient and facile regioselective synthesis of new substituted (E)-1-(3-aryl-7,8-dihydrocinnoline-5(6H)-ylidene)hydrazines and (1E,2E)-1,2-bis(3-aryl-7,8-dihydrocinnoline-5(6H)-ylidene)hydrazines. J IRAN CHEM SOC 11, 1067–1074 (2014). https://doi.org/10.1007/s13738-013-0378-2

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Keywords

  • Arylglyoxal
  • Cinnoline
  • 1,3-Cyclohexanedione
  • Dimedone
  • One-pot
  • Regioselective