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Synthesis of substituted quinolinone ketones derived with some five, six and seven-membered heterocycles

Year 2016, Volume: 3 Issue: 1, 27 - 45, 11.01.2016

Abstract

Abstract: The synthesis of a series of new quinolinyl ketones substituted with some five, six and seven-membered diaza-heterocycles is described. Efficient base or acid-catalyzed nucleophilic heterocyclization of 6-ethyl-4,5-dioxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxaldehyde with a variety of nitrogen and/or carbon 1,2-, 1,3-, and 1,4-binucleophiles afforded the target ketones in good yields. The structure of all new products was established on basis of their spectral and analytical data.

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  • Abood, N.; AL-Hilfi, J. A . “Theoretical NMR investigation of pyrazol and substituted pyrazoles, DNMR and 1H spin-lattice relaxation times”, The First Scientific Conference the Collage of Sciences 2013, 340–350. www.iasj.net/iasj?func=fulltext&aId=77147.
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Year 2016, Volume: 3 Issue: 1, 27 - 45, 11.01.2016

Abstract

References

  • Gharib, A.; Jahangir, M. Org. Chem. Inter. 2013, 1–7; http://dx.doi.org/10.1155/2013/693763.
  • Abass, M.; Mostafa, B. B. Bioorg. Med. Chem. 2005, 13, 6133–6144.
  • El-Shennawy, A. M.; Mohamed, A. H.; Abass, M. Medscape Gen. Med. 2007, 9, 15–33.
  • El-Shennawy, A.; Abass, M.; Mostafa, A. New Egypt. J. Med. 2009, 40, 308–312.
  • El-Shennawy, A. A. M.; Hammam, O. A.; Abass, M.; Eman,A. New Egypt. J. Med. 2008, 39, 573–580.
  • Abass, M.; Othman, E. S. Res. Chem. Intermed. 2013, 1–9; DOI: 10.1007/s111164-013-1174-4.
  • Khodairy, A.; Abass, M. Chem. Heterocycl. Compds. 2011, 47, 611–621.
  • Abass, M., Phosphorus, Sulfur, Silicon 2007, 182, 735–748.
  • Duraipandiyan, V.; Ignacimuthu S. J. Ethnopharm. 2009, 123, 494–498.
  • Tavares, L. C.; Johann, S.; Alves, T. M. A.; Guerra, J. C.; Souza-Fagundes, E. M.; Cisalpino, P. S.; Bortoluzzi, A. J.; Caramori, G. F.; Piccoli, R. M.; Braibante, H. T. S.; et al. Eur. J. Med. Chem. 2011, 46, 4448–4456.
  • Kalkhambkar, R. G.; Aridoss, G.; Kulkarni, G. M.; Bapset, R. M.; Mudaraddi, T. Y.; Premkumar, N.; Jeong, Y. T. Monatsh. Chem. 2011, 142, 305–315.
  • Slambrouck, S. V.; Steelant, W. F. A.; Evdokimov, N. M.; Uglinskii, P. Y.; Elias, E. M.; et al. J. Med. Chem. 2008, 51, 2561–2570.
  • Guo, R. H.; Zhang, Q.; Ma, Y.B.; Huang, X. Y.; Luo, J.; Wang, L. J; Geng, C. A.; Zhang, X. M.; Zhou, J.; Jiang, Z. Y.; et al. Bioorg. Med. Chem. 2011, 19, 1400–1408.
  • Guo, R. H.; Zhang, Q.; Ma,Y. B.; Luo, J.; Geng, C. A.; Wang, L. J.; Zhang, X. M.; Zhou, J.; Jiang, Z. Y.; Chen. J. J. Eur. J. Med. Chem. 2011, 46, 307–319.
  • Ibrahim, M. A.; Ali, T. E.; El-Kazak, A. M.; Mohamed A. M. Heterocycles 2013, 87, 1075–1086.
  • Ibrahim, M. A.; Ali, T. E.; El-Kazak, A. M.; Mohamed A. M. J. Heterocycl. Chem. 2014; DOI: 10.1002/jhet.2195.
  • Ibrahim, M. A. J. Braz. Chem. Soc. 2013, 24, 1754–1763.
  • Ibrahim M. A.; El-Gohary, N. M. Heterocycles 2014, 89,
  • –425.
  • Curreli, F.; Zhang, H.; Zhang, X.; Pyatkin, I.; Victor, Z.; Altieri, A.; Debnath, A. K. Bioorg. Med. Chem. 2011, 19, 77–90.
  • Plaskon, A. S.; Grygorenko, O. O.; Ryabukhin, S. V.Tetrahedron 2012, 68, 2743–2757.
  • Musthafa, T. N. M.; Siddiqui, Z. N.; Husain, F. M.; Ahmad, I. Med. Chem. Res. 2011, 20, 1473–1481.
  • Ibrahim, M. A.; Ali, T. E.; El-Gohary, N. M.; El‐Kazak, A. M. Eur. J. Chem.2013, 4, 311–328.
  • Ibrahim, M. A.; Abdel-Hamed, M. A. M.; El-Gohary, N. M. J. Braz. Chem. Soc. 2011, 22, 1130–1139.
  • Ibrahim, M. A. Arkivoc 2008, 192–204.
  • Ibrahim, M. A. Tetrahedron 2013, 69, 6861–6865.
  • Singh, G.; Singh, G.; Ishar, M. P. S. Synlett 2003, 256–258.
  • Ibrahim, M. A.; Hassanin, H. M.; Abass, M.; Badran, S. Arkivoc 2013, 424–431.
  • Sabitha, G. Aldrichimica Acta 1996, 29, 15–25.
  • Abass, M.; Abdel-Megid, M.; Hassan, M. Synth. Commun. 2007, 37, 329–352.
  • Abass, M.; Mohamed, E. A.; Mayas, A. S.; Ibrahim, A. H. J. Chem. Sci. 2012, 124, 1033–1041.
  • Hatzade, K. M.; Taile, V. S.; Gaidhane, P. K.; Umare, V. D.; Haldar, A. G. M.; Ingle, V. N. Indian J. Chem.2009, 48B, 1548–1557.
  • Kurasawa, Y.; Takano, A.; Kato, K.; Takada, A.; Kim, H. S.; Okamoto, Y. J. Heterocycl. Chem. 1996, 33. 421–425.
  • Escolástico, C.; Blanco, M.; Claramunt, R. M.; Sanz, D.; Elguero, J. Open Org. Chem. J. 2008, 2, 10–16.
  • Gray, E. J.; Stevens, M. F. G. J. Chem. Soc.Perkin Trans. 1, 1976, 1492–1496.
  • Abood, N.; AL-Hilfi, J. A . “Theoretical NMR investigation of pyrazol and substituted pyrazoles, DNMR and 1H spin-lattice relaxation times”, The First Scientific Conference the Collage of Sciences 2013, 340–350. www.iasj.net/iasj?func=fulltext&aId=77147.
  • Burno, O.; Schenone, S.; Ranise, A.; Bondavalli, F.; Barocelli, E.; Ballabeni, V.; Chiavarini, M.; Bertoni, S.; Tognolini, M.; Impicciatore, M. Bioorg. Med. Chem. 2001, 9, 629–636.
  • Abass, M.; Othman, E. S.; Hassan, A. Synth. Commun. 2007, 37, 607–621.
  • Silverstein, R. M.; Bassler, C. G.; Morrill, T. C. “Spectroscopic Identification of organic Compounds”, 3rd Edn., Wiley International Edition, New York, 1974.
  • Marco-Contelles, J.; Perez-Mayoral, E.; Samadi, A.; Carreiras, M. C.; Soriano, E. Chem. Rev. 2009, 109, 2652–2671.
There are 40 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Magdi Ahmed This is me

Hany Hassanin

Mohamed Abass

Shimaa Badran This is me

Publication Date January 11, 2016
Submission Date December 10, 2015
Published in Issue Year 2016 Volume: 3 Issue: 1

Cite

Vancouver Ahmed M, Hassanin H, Abass M, Badran S. Synthesis of substituted quinolinone ketones derived with some five, six and seven-membered heterocycles. JOTCSA. 2016;3(1):27-45.