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Synthesis of functionally substituted isoxazole and isothiazole derivatives

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Abstract

Acylation of benzene and toluene with 5-phenyl- and 5-(p-tolyl)isoxazole-3-carbonyl chlorides gave 5-phenyl(or p-tolyl)isoxazol-3-yl phenyl(or p-tolyl)ketones which were reduced to the corresponding alcohols with sodium tetrahydridoborate in propan-2-ol. Selective reduction of the carboxy group in 4,5-dichloroisothiazole-3-carboxylic acid was achieved by the action of BH3, and the aldehyde group in 4-formyl-2-methoxyphenyl 5-arylisoxazole-3-carboxylates and 4,5-dichloroisothiazole-3-carboxylates was reduced to hydroxymethyl group with sodium triacetoxyhydridoborate in benzene. Acylation of the resulting hydroxymethyl derivatives with 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carbonyl chlorides afforded the corresponding esters containing two azole fragments in their molecules.

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References

  1. Murugesan, N., Gu, Z., Spergel, S., Young, M., Chen, P., Mathur, A., Leith, L., Hermsmeier, M., Liu, E.C., Zhang, R., Bird, E., Waldron, T., Marino, A., Koplowitz, B., Humphreys, W.G., Chong, S., Morrison, R.A., Webb, M.L., Moreland, S., Trippodo, N., and Barrish, J.C., J. Med. Chem., 2003, vol. 46, p. 125; Gardner, T.S., Wenis, E., and Lee, J., J. Med. Chem., 1959, vol. 2, p. 133; Pinto, P. and Dougados, M., Acta Reumatol. Port., 2006, vol. 31, p. 215; Talley, J.J., Brown, D.L., Carter, J.S., Graneto, M.J., Koboldt, C.M., Masferrer, J.L., Perkins, W.E., Rogers, R.S., Shaffer, A.F., Zhang, Y.Y., Zweifel, B.S., and Seibert, K., J. Med. Chem., 2000, vol. 43, p. 775.

    Article  CAS  Google Scholar 

  2. Shailaja, M., Manjula, A., and Vittal Rao, B., Indian J. Chem., Sect. B, 2011, vol. 50, p. 214; Rzeski, W., Ikonomidou, Ch. and Turski, L., Biochem. Pharmacol., 2002, vol. 64, p. 1195; Kamal, A., Bharathi, E.V., Reddy, J.S., Ramaiah, M.J., Dastagiri, D., Reddy, K., Viswanath, A., Reddy, T.L., Shaik, T.B., Pushpavalli, S.N.C.V.L., and Bhadra, M.P., Eur. J. Med. Chem., 2011, vol. 46, p. 691.

    Google Scholar 

  3. Clerici, F., Gelmi, M.L., Pellegrino, S., and Pocar, D., Bioactive Heterocycles III, Khan, M.T.H., Ed., Berlin: Springer, 2007, p. 179.

  4. Beebe, J.S., Jani, J.P., Knauth, E., Goodwin, P., Higdon, C., Rossi, A.M., Emerson, E., Finkelstein, M., Floyd, E., Harriman, S., Atherton, J., Hillerman, S., Soderstrom, C., Kou, K., Gant, T., Noe, M.C., Foster, B., Rastinejad, F., Marx, M.A., Schaeffer, T., Whalen, P.M., and Roberts, W.G., Cancer Res., 2003, vol. 63, p. 7301.

    CAS  Google Scholar 

  5. Kulchitsky, V.A., Potkin, V.I., Zubenko, Yu.S., Chernov, A.N., Talabaev, M.V., Demidchik, Yu.E., Petkevich, S.K., Kazbanov, V.V., Gurinovich, T.A., Roeva, M.O., Grigoriev, D.G., Kletskov, A.V., and Kalunov, V.N., Med. Chem., 2012, vol. 8, p. 22.

    Article  CAS  Google Scholar 

  6. Potkin, V.I., Dikusar, E.A., and Petkevich, S.K., Dokl. Nats. Akad. Navuk Belarusi, 2008, vol. 52, p. 60.

    CAS  Google Scholar 

  7. Potkin, V.I., Gadzhily, R.A., Dikusar, E.A., Petkevich, S.K., Zhukovskaya, N.A., Aliev, A.G., and Nagieva, Sh.F., Russ. J. Org. Chem., 2012, vol. 48, p. 127.

    Article  CAS  Google Scholar 

  8. Potkin, V.I., Kletskov, A.V., Petkevich, S.K., Khotyanovich, M.O., Zubenko, Yu.S., and Kul’chitskii, V.A., Russ. J. Org. Chem., 2013, vol. 49, p. 283.

    Article  CAS  Google Scholar 

  9. Dikusar, E.A., Nechai, N.I., Potkin, V.I., Kaberdin, R.V., Kozlov, N.G., and Kovganko, N.V., Khim. Prirodn. Soedin., 2003, vol. 39, p. 186; Potkin, V.I., Zubenko, Yu.S., Bykhovetz, A.I., Zolotar, R.M., and Goncharuk, V.M., Nat. Prod. Commun., 2009, vol. 4, p. 1205.

    CAS  Google Scholar 

  10. Nechai, N.I., Dikusar, E.A., Potkin, V.I., and Kaberdin, R.V., Russ. J. Org. Chem., 2004, vol. 40, p. 1009.

    Article  CAS  Google Scholar 

  11. Zapol’skii, V.A., Namyslo, J.C., de Meijere, A., and Kaufmann, D.E., Beilst. J. Org. Chem., 2012, vol. 8, p. 621.

    Article  Google Scholar 

  12. Takhistov, V.V., Prakticheskaya mass-spektrometriya organicheskikh soedinenii (Practical Mass Spectrometry of Organic Compounds), Leningrad: Leningr. Gos. Univ., 1977, p. 265; Takhistov, V.V., Rodin, A.A., and Maksimova, B.N., Usp. Khim., 1991, vol. 60, p. 2143.

    Google Scholar 

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    V. I. Potkin, S. K. Petkevich, A. V. Kletskov, E. A. Dikusar, Yu. S. Zubenko & N. A. Zhukovskaya

  2. Institute of Physiology, National Academy of Sciences of Belarus, Minsk, Belarus

    V. V. Kazbanov & S. G. Pashkevich

Authors
  1. V. I. Potkin
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  2. S. K. Petkevich
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  3. A. V. Kletskov
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  4. E. A. Dikusar
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  5. Yu. S. Zubenko
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  6. N. A. Zhukovskaya
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  7. V. V. Kazbanov
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  8. S. G. Pashkevich
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Correspondence to V. I. Potkin.

Additional information

Original Russian Text © V.I. Potkin, S.K. Petkevich, A.V. Kletskov, E.A. Dikusar, Yu.S. Zubenko, N.A. Zhukovskaya, V.V. Kazbanov, S.G. Pashkevich, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 10, pp. 1543–1553.

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Potkin, V.I., Petkevich, S.K., Kletskov, A.V. et al. Synthesis of functionally substituted isoxazole and isothiazole derivatives. Russ J Org Chem 49, 1523–1533 (2013). https://doi.org/10.1134/S1070428013100205

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  • DOI: https://doi.org/10.1134/S1070428013100205

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