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Reactions of hydroxyphenyl-substituted 1,2,4-triazoles with electrophylic reagents

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Abstract

Reactions of hydroxyphenyl substituted 1,2,4-triazoles with various electrophylic reagents were studied. Despite of the presence of several nucleophilic centers in the molecule, the reactions were shown to proceed regioselectively, with the formation of N-substituted 3-(2-hydroxyphenyl)-1,2,4-triazoles. As a result of the reactions of alkylation, tosylation, sulfoamination and aminomethylation by Mannich reaction earlier unknown potential biologically active N-derivatives of 1,2,4-triazole were obtained.

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References

  1. Shering, A.G., FRG Patent no. 2936951, 1981; Chem.Abstrs., 1982, vol. 96, p. 52509.

  2. Bayer A.G., FRG Patent no. 2936951, 1975; Chem. Abstrs., 1975, vol. 83, p. 206290.

  3. Ryabukhin, Yu.I., Doctoral Sci. (Chem.) Dissertation, Nauk. Rostov-on-Don, 1991.

  4. Ryabukhin, Yu.I., Mezheritskii, V.V., Karpenko, V.D., and Dorofeenko, G.N., Khim. Geterotsikl. Soed., 1975, no. 9, p. 1184.

  5. Dorofeenko, G.N., Ryabukhin, Yu.I., Bulgarevich, S.B., Mezheritskii, V.V., and Ryabukhina, O.Yu., Zh. Org. Khim., 1977, vol. 13, no. 11, p. 2459.

    Google Scholar 

  6. Suvorova, E.Yu., Vikrishchuk, N.I., Popov, L.D., Starikova, Z.A., Vikrishchuk, A.D., and Zhdanov, Yu.A., Zh. Org. Khim., 2007, vol. 43, no. 10, p. 1556.

    Google Scholar 

  7. Kompan, O.E., Gerr, R.G., Struchkov, Yu.T., Faleeva, L.N., Ryabukhin, Yu.I., Olekhnovich, L.P., Khim. Geterotsikl. Soed, 1989, no. 1, p. 109.

  8. Emsli, D., Finei, D., and Satklif, L., Spektroskopiya yadernogo magnitnogo rezonansa vysokogo razresheniya (High Resolution NMR Spectroscopy), Moscow: Mir, 1968, p. 514.

    Google Scholar 

  9. Mashkovskii, M.D., Lekarstvennye sredstva (Renedies), Moscow: Meditsina, 1972, p. 368.

    Google Scholar 

  10. Fukuzumi, K., Ikeda, N., and Egawa, M., J. Am. Oil Chem. Soc. 1976, vol. 53, p. 623.

    Article  CAS  Google Scholar 

  11. Nagy, S., Argyclan, G., Molnar, J., Kawase, M., and Motohashi, N., Anticancer Res., 1996, vol. 16, p. 1916.

    Google Scholar 

  12. Moosman, B., Skutella, T., Beyer, K., and Behl, C., Biol. Chem., 2001, vol. 382, p. 1601.

    Article  Google Scholar 

  13. Korth, C., May, B., Cohen, F.E., and Prusiner, S.B., Proc. Natl. Acad. Sci. U. S., 2001, vol. 98, p. 9836.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Chemical Faculty, Southern Federal University, ul. Zorge 7, Rostov-on-Don, 344090, Russia

    E. Yu. Shasheva, N. I. Vikrishchuk, L. D. Popov & M. E. Kletskii

  2. Southern Scientific Center of Science of the Russian Academy of Sciences, Rostov-on-Don, Russia

    A. D. Vikrishchuk & I. E. Mikhailov

  3. Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of Sciences, Moscow, Russia

    K. A. Lysenko

Authors
  1. E. Yu. Shasheva
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  2. N. I. Vikrishchuk
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  3. L. D. Popov
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  4. A. D. Vikrishchuk
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  5. I. E. Mikhailov
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  6. K. A. Lysenko
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  7. M. E. Kletskii
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Corresponding author

Correspondence to E. Yu. Shasheva.

Additional information

Original Russian Text © E.Yu. Shasheva, N.I. Vikrishchuk, L.D. Popov, A.D. Vikrishchuk, I.E. Mikhailov, K.A. Lysenko, M.E. Kletskii, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 10, pp. 1739–1748.

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Shasheva, E.Y., Vikrishchuk, N.I., Popov, L.D. et al. Reactions of hydroxyphenyl-substituted 1,2,4-triazoles with electrophylic reagents. Russ J Gen Chem 79, 2234–2243 (2009). https://doi.org/10.1134/S1070363209100259

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  • DOI: https://doi.org/10.1134/S1070363209100259

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