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Optimization of the Reaction Conditions for Synthesis of 3-(Aryloxy)quinoline Derivatives via Friedländer's Cyclization Reaction

  • 투고 : 2013.01.09
  • 심사 : 2013.03.31
  • 발행 : 2013.06.20

초록

6,7-Dimethoxy-2-methyl-3-(4-nitrophenoxy)quinoline was synthesized by Friedl$\ddot{a}$nder's cyclization reaction. Different bases and solvents were tested in order to optimize the reaction conditions. The highest yields were obtained using piperidine in refluxing ethanol. Further reactions were carried out in order to prepare different diarylamide and diarylurea derivatives in moderate to high yields in order to examine their anticancer activities.

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참고문헌

  1. Chauhan, P. M. S.; Srivastava, S. K. Curr. Med. Chem. 2001, 8, 1535. https://doi.org/10.2174/0929867013371851
  2. Roma, G.; Braccio, M. D.; Grossi, G.; Mattioli, F.; Ghia, M. Eur. J. Med. Chem. 2000, 35, 1021. https://doi.org/10.1016/S0223-5234(00)01175-2
  3. Kalluraya, B.; Sreenivasa, S. Farmaco 1998, 53, 399. https://doi.org/10.1016/S0014-827X(98)00037-8
  4. Dube, D.; Blouin, M.; Brideau, C.; Chan, C. C.; Desmarais, S.; Ethier, D.; Falgueyret, J. P.; Friesen, R. W.; Girard, M.; Girard, Y.; Guay, J.; Riendeau, D.; Tagari, P.; Young, R. N. Bioorg. Med. Chem. Lett. 1998, 8, 1255. https://doi.org/10.1016/S0960-894X(98)00201-7
  5. Jain, K. S.; Bariwal, J. B.; Kathiravan, M. K.; Phoujdar, M. S.; Sahne, R. S.; Chauhan, B. S.; Shah, A. K.; Yadav, M. R. Bioorg. Med. Chem. Lett. 2008, 16, 4759. https://doi.org/10.1016/j.bmc.2008.02.091
  6. Hoemann, M. Z.; Kumaravel, H. G.; Xie, R. L.; Rossi, R. F.; Meyer, S.; Sidhu, A.; Cuny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2000, 10, 2675. https://doi.org/10.1016/S0960-894X(00)00542-4
  7. Wang, X.-J.; Gong, D.-L.; Wang, J.-D.; Zhang, J.; Liu, C.-X.; Xiang, W.-S. Bioorg. Med. Chem. Lett. 2011, 21, 2313. https://doi.org/10.1016/j.bmcl.2011.02.095
  8. Hayat, F.; Moseley, E.; Salahuddin, A.; Van Zyl, R. L.; Azam, A. Eur. J. Med. Chem. 2011, 46, 1897. https://doi.org/10.1016/j.ejmech.2011.02.004
  9. Palde, P. B.; Gareiss, P. C.; Miller, B. L. J. Am. Chem. Soc. 2008, 130, 9566. https://doi.org/10.1021/ja802229f
  10. Jenekhe, S. A.; Lu, L.; Alam, M. M. Macromolecules 2001, 34, 7315. https://doi.org/10.1021/ma0100448
  11. Kouznetsov, V. V.; Vargas Mendez, L. Y.; Melendez Gomez, C. M. Curr. Org. Chem. 2005, 9, 141. https://doi.org/10.2174/1385272053369196
  12. Marco-Contelles, J.; Perez-Mayoral, E.; Samadi, A.; do Carmo Carreiras, M.; Soriano, E. Chem. Rev. 2009, 109, 2652. https://doi.org/10.1021/cr800482c
  13. Cheng, C. C.; Yan, S. J. Org. React. 1982, 28, 37.
  14. Thummel, R. P. Synlett 1992, 1.
  15. Gladiali, S.; Chelucci, G.; Mudadu, M. S.; Gastaut, M. A.; Thummel, R. P. J. Org. Chem. 2001, 66, 400. https://doi.org/10.1021/jo0009806
  16. NCI website, www.dtp.nci.nih.gov.

피인용 문헌

  1. ChemInform Abstract: Optimization of the Reaction Conditions for Synthesis of 3-(Aryloxy)quinoline Derivatives via Friedlaender′s Cyclization Reaction. vol.44, pp.41, 2013, https://doi.org/10.1002/chin.201341169