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Substituted quinolinones. 18. 3-Acetyl-4-methylthioquinolin-2(1H)-one as useful synthon intermediate for synthesis of some new quinolinones

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Abstract

3-Acetyl-4-methylthioquinolin-2(1H)-one (3) has been prepared and its reactivity towards treatment with different reagents, dilute sulfuric acid, aqueous sodium hydroxide, and hydrogen peroxide, is described. The reactions of compound 3 with benzylamine, benzaldehyde, DMF-DMA, Vilsmeier-Haack reagent, 2-chloro-3-formyl-pyridopyrimidone and malononitrile have been carried out under convenient conditions. Compound 3 underwent heterocyclization reactions with some binucleophiles, hydrazine, hydroxylamine, urea, thiourea, semicarbazide, and thiosemicarbazide, furnishing some known five, six, and seven heterocyclic annellated quinolines. All the new compounds have been characterized using different spectral and analytical tools.

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References

  1. M. Abass, B.B. Mostafa, Bioorg. Med. Chem. 13, 6133 (2005)

    Article  CAS  Google Scholar 

  2. M. Abass, Phosphorus Sulfur Silicon 182, 735 (2007)

    Article  CAS  Google Scholar 

  3. A.M. El-Shennawy, A.H. Mohamed, M. Abass, Medscape Gen. Med. 9, 15 (2007)

    Google Scholar 

  4. A.M. El-Shennawy, O.A. Hammam, M. Abass, A. Eman, New Egypt. J. Med. 39, 573 (2008)

    Google Scholar 

  5. A.M. El-Shennawy, M. Abass, A. Mostafa, New Egypt. J. Med. 40, 308 (2009)

    Google Scholar 

  6. G.C. Muscia, M. Bollini, A.M. Bruno, S.E. Asis, J. Chil. Chem. Soc. 51, 859 (2006)

    Article  CAS  Google Scholar 

  7. H. Nakamura, H. Ohki, A. Yamada, K. Kawabata, WO Patent no 95/06047. March 2, 1995

  8. A. Foroumadi, S. Emami, M. Mehni, M.H. Moshafi, A. Shafiee, Bioorg. Med. Chem. Lett. 15, 4536 (2005)

    Article  CAS  Google Scholar 

  9. G. Bolakatti, M.S. Katagi, S.N. Mamledesai, M.L. Sujatha, P. Dabadi, N. Miskin, RGUHS J. Pharm. Sci. 2, 60 (2012)

    Article  Google Scholar 

  10. A. Aubry, N. Veziris, E. Cambau, C. Truffot-Pernot, V. Jarlier, L.M. Fisher, Antimicrob. Agents Chemother. 50, 104 (2006)

    Article  CAS  Google Scholar 

  11. A. Detsi, D. Bouloumbasi, K.C. Prousis, M. Koufaki, G. Athanasellis, G. Melagraki, A. Afantitis, O. Igglessi-Markopoulou, C. Kontogiorgis, D.J. Hadjipavlou-Litina, J. Med. Chem. 50, 2450 (2007)

    Article  CAS  Google Scholar 

  12. B.S. Jayashree, S. Thomas, Y. Nayak, Med. Chem. Res. 19, 193 (2010)

    Article  CAS  Google Scholar 

  13. R. Tedesco, A.N. Shaw, R. Bambal, D. Chai, N.O. Concha, M.G. Darcy, D. Dhanak, D.M. Fitch, A. Gates, W.G. Gerhardt, D.L. Halegoua, C. Han, G.A. Hofmann, V.K. Johnston, A.C. Kaura, N. Liu, R.M. Keenan, J. Lin-Goerke, R.T. Sarisky, K.J. Wiggall, M.N. Zimmerman, K.J. Duffy, J. Med. Chem. 49, 971 (2006)

    Article  CAS  Google Scholar 

  14. P. Cheng, Q. Zhang, Y.-B. Ma, Z.-Y. Jiang, X.-M. Zhang, F.-X. Zhang, J.-J. Chen, Bioorg. Med. Chem. Lett. 18, 3787 (2008)

    Article  CAS  Google Scholar 

  15. J.M. Kraus, H.B. Tatipaka, S.A. McGuffin, N.K. Chennamaneni, M. Karimi, J. Arif, C.L.M.J. Verlinde, F.S. Buckner, M.H. Gelb, J. Med. Chem. 53, 3887 (2010)

    Article  CAS  Google Scholar 

  16. B. Joseph, F. Darro, A. Béhard, B. Lesur, F. Collignon, C. Decaestecker, A. Frydman, G. Guillaumet, R. Kiss, J. Med. Chem. 45, 2543 (2002)

    Article  CAS  Google Scholar 

  17. E. Martinborough, Y. Shen, A. van Oeveren, Y.O. Long, T.L.S. Lau, K.B. Marschke, W.Y. Chang, F.J. López, E.G. Vajda, P.J. Rix, O.H. Viveros, A. Negro-Vilar, L. Zhi, J. Med. Chem. 50, 5049 (2007)

    Article  CAS  Google Scholar 

  18. R.J. DeVita, T.F. Walsh, J.R. Young, J. Jiang, F. Ujjainwalla, R.B. Toupence, M. Parikh, S.X. Huang, J.A. Fair, M.T. Goulet, M.J. Wyvratt, J.-L. Lo, N. Ren, J.B. Yudkovitz, Y.T. Yang, K. Cheng, J. Cui, G. Mount, S.P. Rohrer, J.M. Schaeffer, L. Rhodes, J.E. Drisko, E. McGowan, D.E. MacIntyre, S. Vincent, J.R. Carlin, J. Cameron, R.G. Smith, J. Med. Chem. 44, 917 (2001)

  19. K.H. Raitio, J.R. Savinainen, J. Vepsäläinen, J.T. Laitinen, A. Poso, T. Järvinen, T. Nevalainen, J. Med. Chem. 49, 2022 (2007)

    Article  Google Scholar 

  20. W. Zhong, H. Liu, M.R. Kaller, C. Henley, E. Magal, T. Nguyen, T.D. Osslund, D. Powers, R.M. Rzasa, H.-L. Wang, W. Wang, X. Xiong, J. Zhang, M.H. Norman, Bioorg. Med. Chem. Lett. 17, 5384 (2007)

    Article  CAS  Google Scholar 

  21. E. Baston, A. Palusczak, R.W. Hartmann, Eur. J. Med. Chem. 35, 931 (2000)

    Article  CAS  Google Scholar 

  22. M.-A. Letellier, J. Guillard, D.-H. Caignard, G. Ferry, J.A. Boutin, M.-C. Viaud-Massuard, Eur. J. Med. Chem. 43, 1730 (2008)

    Article  CAS  Google Scholar 

  23. I.-L. Chen, K.-M. Chang, C.-L. Miaw, C.-H. Liao, J.-J. Chen, T.-C. Wang, Bioorg. Med. Chem. 15, 6527 (2007)

    Article  CAS  Google Scholar 

  24. M. Abass, M.M. Ismail, W.R. Abdel-Monem, A.S. Mayas, Chem. Papers 64, 72 (2009)

    Article  Google Scholar 

  25. A.M.F. Elgohary, M.M. Hassan, M. Abass, Pharm. Chem. 3, 1 (2011)

    CAS  Google Scholar 

  26. C. S. Pak, E. B. Choi. Synthesis, 1291 (1992)

  27. C. S. Pak, E. B. Choi, H. C. Yang, G. H. Yon, G. H. Lee, H. K. Lee, S. K. Kim, Y. S. Lee, K. W. Lee, Y. R. Chung, H. T. Kim, U.S. Patent 5,430,153, Jul. 4, 1995

  28. I. V. Ukrainets, L. V. Sidorenko, O. V. Gorokhova, S. V. Slobodzyan, Chem. Heterocycl. Comp., 42, 882 (2006); (Translated from Khim. Geterotsikl. Soedin., 1022 (2006))

    Google Scholar 

  29. S. Sarveswari, T.K. Raja, R. Vijayaraghavan, T. Narasimhamurthy, R.S. Rathore, Acta Cryst. E63, o4600–o4601 (2007)

    CAS  Google Scholar 

  30. A. Nohara, T. Umetani, Y. Sanno, Tetrahedron 30, 3553 (1974)

    Article  CAS  Google Scholar 

  31. T. George, D.V. Mehta, D.A. Dabholkar, J. Org. Chem. 36, 2192 (1971)

    Article  CAS  Google Scholar 

  32. M. Sankaran, C. Kumarasamy, U. Chokkalingam, P.S. Mohan, Bioorg. Med. Chem. Lett. 20, 7147 (2010)

    Article  CAS  Google Scholar 

  33. E.J. Brnardic, R.M. Garbaccio, M.E. Fraley, E.S. Tasber, J.T. Steen, K.L. Arrington, V.Y. Dudkin, G.D. Hartman, S.M. Stirdivant, B.A. Drakas, K. Rickert, E.S. Walsh, K. Hamilton, C.A. Buser, J. Hardwick, W. Tao, S.C. Beck, X. Mao, R.B. Lobell, L. Sepp-Lorenzino, Y. Yan, M. Ikuta, S.K. Munshi, L.C. Kuo, C. Kreatsoulas, Bioorg. Med. Chem. Lett. 17, 5989 (2007)

    Article  CAS  Google Scholar 

  34. R. Musiol, J. Jampilek, K. Kralova, J. Finster, D. Tabak, H. Niedbala, J. Csollei, J. Dohnal, J. Polanski, 12th Inter. Electr. Conf. Synth. Org. Chem. (ECSOC-12), 1–30 November 2008, C0012. http://www.usc.es/congresos/ecsoc/12/ECSOC12.htm

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Hassan, M.M., Othman, E.S. & Abass, M. Substituted quinolinones. 18. 3-Acetyl-4-methylthioquinolin-2(1H)-one as useful synthon intermediate for synthesis of some new quinolinones. Res Chem Intermed 39, 1209–1225 (2013). https://doi.org/10.1007/s11164-012-0678-7

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