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Synthesis of 3-substitued 5-(2-thienyl)isoxazoles

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Abstract

The reaction of 3,4,4-trichloro-1-(2-thienyl)but-3-en-1-one with hydroxylamine gave 3-hydroxyiminomethyl-5-(2-thienyl)isoxazole which was converted into 5-(2-thienyl)isoxazole-3-carbonitrile by the action of acetic anhydride in pyridine. 5-(2-Thienyl)isoxazole-3-carbonitrile reacted with hydroxylamine to produce the corresponding amide oxime. Heterocyclization of its O-acyl derivatives in acetic acid afforded 5-substituted 3-[5-(2-thienyl)isoxazol-3-yl]-1,2,4-oxadiazoles.

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References

  1. Yamamoto, T., Fujita, K., Asari, S., Chiba, A., Kataba, Y., Ohsumi, K., Ohmuta, N., Iida, Y., Ijichi, C., Iwayama, S., Fukuchi, N., and Shoji, M., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 3736; Dallanoce, C., Frigerio, F., De Amici, M., Dorsch, S., Klotz, K.N., and De Micheli, C., Bioorg Med Chem., 2007, vol. 15, p. 2533; Hafez, H.N. and El-Gazzar, A.B.A., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 5222; Mel’nikov, N.N., Pestitsidy. Khimiya, tekhnologiya i primenenie (Peticides. Chemistry, Technology, and Application), Moscow: Khimiya, 1987.

    Article  CAS  Google Scholar 

  2. Potkin, V.I., Petkevich, S.K., and Kurman, P.V., Russ. J. Org. Chem., 2010, vol. 46, p. 1305.

    Article  CAS  Google Scholar 

  3. Pohland, A.E. and Benson, W.R., Chem. Rev., 1966, vol. 66, p. 161; Kaberdin, R.V., Potkin, V.I., and Petkevich, S.K., Vestsi Nats. Akad. Navuk Belarusi, Ser. Khim. Navuk, 2006, no. 2, p. 99.

    Article  CAS  Google Scholar 

  4. Petkevich, S.K., Potkin, V.I., and Kaberdin, R.V., Russ. J. Org. Chem., 2004, vol. 40, p. 1146.

    Article  CAS  Google Scholar 

  5. Zil’berman, E.N., Reaktsii nitrilov (Reactions of Nitriles), Moscow: Khimiya, 1972, p. 104.

    Google Scholar 

  6. Chesnyuk, A.A., Mikhailichenko, S.N., Konyushkin, L.D., Firgang, S.I., and Zaplishnyi, V.N., Izv. Ross. Akad. Nauk, Ser. Khim., 2005, p. 1845.

  7. Potkin, V.I., Petkevich, S.K., and Kurman, P.V., Russ. J. Org. Chem., 2009, vol. 45, p. 551.

    Article  CAS  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 & P. V. Kurman

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  1. V. I. Potkin
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  2. S. K. Petkevich
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  3. P. V. Kurman
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Correspondence to V. I. Potkin.

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Original Russian Text © V.I. Potkin, S.K. Petkevich, P.V. Kurman, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 6, pp. 911–914.

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Potkin, V.I., Petkevich, S.K. & Kurman, P.V. Synthesis of 3-substitued 5-(2-thienyl)isoxazoles. Russ J Org Chem 47, 928–932 (2011). https://doi.org/10.1134/S1070428011060169

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  • DOI: https://doi.org/10.1134/S1070428011060169

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