Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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One-Pot Multicomponent Synthetic Route for New Quinolidinyl 2,4-Thiazolidinediones

  • Mali, Jyotirling R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Bhosle, Manisha R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Mahalle, Shital R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Mane, Ramrao A. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
  • Received : 2010.01.30
  • Accepted : 2010.03.20
  • Published : 2010.07.20
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Abstract

A convenient one-pot condensation route has been developed for obtaining 5-[(2-(piperidin-1-yl) quinolin-3-yl) methylene]-2,4-thiazolidinediones using multicomponents, 2-chloro-3-formyl quinolines, piperidine, 2,4-thiazolidinedione and safer medium/mediator, polyethylene glycol-400.

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References

  1. Brown, F. C. Chem. Rev. 1961, 61, 463. https://doi.org/10.1021/cr60213a002
  2. Lesyk, R. B.; Zimenkovsky, B. S. Curr. Org. Chem. 2004, 8, 1547. https://doi.org/10.2174/1385272043369773
  3. Malamas, M. S.; Sredy, J.; Gunawan, I.; Mihan, B.; Sawicki, D. R.; Seestaller, L.; Sullivan, D.; Flam, B. R. J. Med. Chem. 2000, 43, 995. https://doi.org/10.1021/jm990476x
  4. Oguchi, M.; Wada, K.; Honma, H.; Kaneko, A.; Teneko, T.; Sakakibara, S.; Ohsumi, J.; Serizawa, N.; Fujiwara, T.; Horikoshi, H.; Fujita, T. J. Med. Chem. 2000, 43, 3052. https://doi.org/10.1021/jm990522t
  5. Yoshioka, T.; Fujita, T.; Kanai, T.; Aizawa, Y.; Kurumada, T.; Hasegawa, K.; Horikoshi, H. J. Med. Chem. 1989, 32, 421. https://doi.org/10.1021/jm00122a022
  6. Clark, D. A.; Goldstein, S. W.; Volkmann, R. A.; Eggler, J. E.; Holland, G. F.; Hulin, B.; Stevenson, R. W.; Kreutter, D. K.; Gibbs, E. M.; Krupp, M. N.; Merrigan, P.; Kelbaugh, P. L.; Andrews, E. G.; Tickner, D. L.; Suleske, R. T.; Lamphere, C. H.; Rajeckes, F. J.; Kappeler, W. H.; McDermott, R. E.; Hutson, N. J.; Johnson, M. R. J. Med. Chem. 1991, 34, 319. https://doi.org/10.1021/jm00105a050
  7. Momose, Y.; Meguro, K.; Ikeda, H.; Hatanaka, C.; Oi, S.; Sohda, T. Chem. Pharm. Bull. 1991, 39, 1440. https://doi.org/10.1248/cpb.39.1440
  8. Cantello, B. C. C.; Cawthome, M. A.; Haigh, D.; Hindley, R. M.; Smith, S. A.; Thurlby, P. L. Bioorg. Med. Chem. Lett. 1994, 4, 1181. https://doi.org/10.1016/S0960-894X(01)80325-5
  9. Michael, J. P. Nat. Prod. Rep. 2004, 650.
  10. Michael, J. P. Nat. Prod. Rep. 2003, 476.
  11. Craig, J. C.; Person, P. E. J. Med. Chem. 1971, 14, 1221. https://doi.org/10.1021/jm00294a022
  12. Dillard, R. D.; Pavey, D. E.; Benslay, D. N. J. Med. Chem. 1973, 16, 251. https://doi.org/10.1021/jm00261a019
  13. De Souza, M. V.; Pais, K. C.; Kaiser, C. R.; Peralta, M. A.; Ferreira, M. de L.; Lourenço, M. C. Bioorg. Med. Chem. 2009, 17, 1474. https://doi.org/10.1016/j.bmc.2009.01.013
  14. Shi, A.; Nguyen, T. A.; Battina, S. K.; Rana, S.; Takemoto, D. J.; Chiang, P. K.; Hua, D. H. Bioorg. Med. Chem. Lett. 2008, 18, 3364. https://doi.org/10.1016/j.bmcl.2008.04.024
  15. Lohray, B. B.; Bhushan, V.; Reddy, A. S.; Rao, P. B.; Reddy, N. J.; Harikishore, P.; Haritha, N.; Vikramadityan, R. K.; Chakrabarti, R.; Rajugopalan, R.; Katneni, K. J. Med. Chem. 1999, 42, 2569. https://doi.org/10.1021/jm980622j
  16. Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Shivanyuk, N.; Tolmachev, A. A. Synthesis 2007, 2872.
  17. Devi, I.; Baruah, B.; Bhuyan, P. J. Synlett 2006, 2593.
  18. Mali, J. R.; Pratap, U. R.; Netankar, P. D.; Mane, R. A. Tetrahedron Lett. 2009, 50, 5025. https://doi.org/10.1016/j.tetlet.2009.06.086
  19. Mahalle, S.; Ligampalle, D.; Mane, R. Heteroatom Chem. 2009, 20, 151. https://doi.org/10.1002/hc.20528
  20. Nair, V.; Vinod, A. U.; Rajesh, C. J. Org. Chem. 2001, 66, 4427. https://doi.org/10.1021/jo001714v
  21. List, B.; Castello, C. Synlett 2001, 1687.
  22. Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. https://doi.org/10.1021/ol0264814
  23. Yuan, Y.; Li, X.; Ding, K. Org. Lett. 2002, 4, 3309. https://doi.org/10.1021/ol0265822
  24. Cheng, J.-F.; Chen, M.; Arrhenius, T.; Nadzan, A. Tetrahedron Lett. 2002, 43, 6293. https://doi.org/10.1016/S0040-4039(02)01403-X
  25. Bora, U.; Saikia, A.; Boruah, R. C. Org. Lett. 2003, 5, 435. https://doi.org/10.1021/ol020238n
  26. Dallinger, D.; Gorobets, N. Y.; Kappe, C. O. Org. Lett. 2003, 5, 1205. https://doi.org/10.1021/ol034085v

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