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Synthesis of aryl substituted quinones as β-secretase inhibitors: Ligand-free direct arylation of quinones with aryl halides

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Abstract

The simple ligand-free direct arylation of quinones with aryl halides applying Pd(OAc)2 as a catalyst in accordance with Heck reaction was studied. This reaction provided a simple and efficient synthetic approach to efficient inhibitors of β-secretase aryl-substituted quinones.

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References

  1. Babula, P., Mikelova, R., Kizek, R., Havel, L., and Sladky, Z., Ceska Slovens. Farm., 2006, vol. 55, p. 151.

    CAS  Google Scholar 

  2. Koyama, J., Recent Patents Anti-Infect. Drug. Discov., 2006, vols. 1, p. 113.

    Article  CAS  Google Scholar 

  3. Babula, P., Adam, V., Havel, L., and Kizek, R., Ceska Slovens. Farm., 2007, vol. 56, p. 114.

    CAS  Google Scholar 

  4. Verma, R. P., Anti-Cancer Agents Med. Chem., 2006, vol. 6, p. 489.

    Article  CAS  Google Scholar 

  5. Bishop, K.J.M., Klajn, R., and Grzybowski, B.A., Angew. Chem. Int. Ed., 2006, vol. 45, p. 5348.

    Article  CAS  Google Scholar 

  6. Gould, S.J., Chem. Rev., 1997, vol. 97, p. 2499.

    Article  CAS  Google Scholar 

  7. Liu, J.-K., Chem. Rev., 2006, vol. 106, p. 2209.

    Article  CAS  Google Scholar 

  8. Zhang, B., Salituro, G., Szalkowski, D., Li, Z., Zhang, Y., Royo, I., Vitella, D., Diez, M.T., Pelaez, F., Ruby, C., Kendall, R.L., Mao, X., Griffin, P., Calaycay, J., Zierath, J.R., Heck, J.V., Smith, R.G., and Moller, D.E., Science, 1999, vol. 284, p. 974.

    Article  CAS  Google Scholar 

  9. Coleman, R.S., Felpin, F.-X., and Chen, W., J. Org. Chem., 2004, vol. 69, p. 7309.

    Article  CAS  Google Scholar 

  10. Nikolovska-Coleska, Z., Xu, L., Hu, Z., Tomita, Y., Li, P., Roller, P.P., Wang, R., Fang, X., Guo, R., Zhang, M., Lippman, M.E., Yang, D., and Wang, S., J. Med. Chem., 2004, vol. 47, p. 2430.

    Article  CAS  Google Scholar 

  11. Viault, G., Grée, D., Das, S., Yadav, J. S., and Grée, R., Eur. J. Org. Chem., 2011, vol. 7, p. 1233.

    Article  Google Scholar 

  12. Hadden, M.K., Hill, S.A., Davenport, J., Matts, R.L., and Blagg, B.S., Bioorg. Med. Chem., 2009, vol. 37, p. 634.

    Article  Google Scholar 

  13. Citron, M., Neuroscience, 2004, vol. 5, p. 677

    CAS  Google Scholar 

  14. Findeis, M.A., Pharmacol. Ther., 2007, vol. 116, p. 266.

    Article  CAS  Google Scholar 

  15. Ortega, A., Rincón, Á., Jiménez-Aliaga, K.L., Bermejo-Bescós, P., Martín-Aragón, S., Molina, M.T., and Csákÿ, A.G., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 2183.

    Article  CAS  Google Scholar 

  16. Zhang, H.-B., Liu, L., Chen, Y.-J., Wang, D., and Li, C.-J., Adv. Synth. Catal., 2006, vol. 348, p. 229.

    Article  CAS  Google Scholar 

  17. Miyamura, H., Shiramizu, M., Matsubara, R., and Kobayashi, S., Angew. Chem. Int. Ed., 2008, vol. 47, p. 8093.

    Article  CAS  Google Scholar 

  18. Lockner, J.W., Dixon, D.D., Risgaard, R., and Baran, P.S., Org. Lett., 2011, vol. 13, p. 5628.

    Article  CAS  Google Scholar 

  19. Ilangovan, A., Saravanakumar, S., and Malayappasamy, S., Org. Lett., 2013, vol. 15, p. 4968.

    Article  CAS  Google Scholar 

  20. Zhang, S., Song, F., Zhao, D., and You, J. Chem. Commun., 2013, vol. 49, p. 4558.

    Article  CAS  Google Scholar 

  21. Pirrung, M.C., Park, K., and Li, Z., Org. Lett., 2001, vol. 3, p. 365.

    Article  CAS  Google Scholar 

  22. Pirrung, M.C., Deng, L., Li, Z., and Park, K. J. Org. Chem., 2002, vol. 67, p. 8374.

    Article  CAS  Google Scholar 

  23. Knölker, H.-J., Fröhner, W., and Reddy, K.R., Synthesis, 2002, p. 557.

    Google Scholar 

  24. Yadav, J.S., Reddy, B.V.S., and Swamy, T., Tetrahedron Lett., 2003, vol. 44, p. 9121.

    Article  CAS  Google Scholar 

  25. Honraedt, A., Callonnec, F.L., Grognec, E.L., Fernandez, V., and Felpin, F.-X., J. Org. Chem., 2013, vol. 78, p. 4604.

    Article  CAS  Google Scholar 

  26. Molina, M.T., Navarro, C., Moreno, A., and Csaky, A.G., Org. Lett., 2009, vol. 11, p. 4938.

    Article  CAS  Google Scholar 

  27. Demchuk, O.M., and Pietrusiewicz, K.M., Synlett, 2009, vol. 7, p. 1149.

    Article  Google Scholar 

  28. Fujiwara, Y., Domingo, V., Seiple, I.B., Gianatassio, R., Bel, M.D., and Baran, P.S., J. Am. Chem. Soc., 2011, vol. 133, p. 3292.

    Article  CAS  Google Scholar 

  29. Wang, J., Wang, S., Wang, G., Zhang, J., and Yu, X.-Q., Chem. Commun., 2012, vol. 48, p. 11769.

    Article  CAS  Google Scholar 

  30. Singh, P.P., Aithagani, S.K., Yadav, M., Singh, V.P., and Vishwakarma, R.A., J. Org. Chem., 2013, vol. 78, p. 2639.

    Article  CAS  Google Scholar 

  31. Komeyama, K., Kashihara, T., and Takaki, K., Tetrahedron Lett., 2013, vol. 54, p. 1084.

    Article  CAS  Google Scholar 

  32. Deb, A., Manna, S., Maji, A., Dutta, U., and Maiti, D., Eur. J. Org. Chem., 2013, p. 5251.

    Google Scholar 

  33. Negishi, E., Coperet, C., Ma, S., Liou, S.-Y., and Liu, F., Chem. Rev., 1996, vol. 96, p. 365.

    Article  CAS  Google Scholar 

  34. Beletskaya, I.P., and Cheprakov, A.V., Chem. Rev., 2000, vol. 100, p. 3009.

    Article  CAS  Google Scholar 

  35. Yang, W., Wang, D., Song, Q., Zhang, S., Wang, Q., and Ding, Y., Organometallics, 2013, vol. 32, p. 4130.

    Article  CAS  Google Scholar 

  36. Li, L., Wu, F., Zhang, S., Wang, D., Ding, Y., and Zhu, Z., Dalton Trans., 2013, vol. 42, p. 4539.

    Article  CAS  Google Scholar 

  37. Zhang, S., and Ding, Y., Organometallics, 2011, vol. 30, p. 633.

    Article  CAS  Google Scholar 

  38. Zhang, S., Shi, L., and Ding, Y., J. Am. Chem. Soc., 2011, vol. 133, p. 20218.

    Article  CAS  Google Scholar 

  39. Yang, W., Zhang, S., Ding, Y., Shi, L., and Song, Q., Chem. Commun., 2011, vol. 47, p. 5310.

    Article  CAS  Google Scholar 

  40. Wang, D., Cai, R., Sharma, S., Jirak, J., Thummanapelli, S.K., Akhmedov, N.G., Zhang, H., Liu, X., Petersen, J.L., Shi, X., J. Am. Chem. Soc., 2012, vol. 134, p. 9012.

    Article  CAS  Google Scholar 

  41. Wang, D., Lu, S., and Zhou, Y., Tetrahedron Lett., 2009, vol. 50, p. 1282.

    Article  CAS  Google Scholar 

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Correspondence to Dawei Wang.

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Wang, D., Ge, B., Yang, S. et al. Synthesis of aryl substituted quinones as β-secretase inhibitors: Ligand-free direct arylation of quinones with aryl halides. Russ J Gen Chem 84, 1615–1621 (2014). https://doi.org/10.1134/S1070363214080295

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  • DOI: https://doi.org/10.1134/S1070363214080295

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