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Nucleophilic substitution in the series of (1,2,3-triazol-1-yl)-1,2,5-oxadiazoles. Reactions with N-, O-, and S-nucleophiles

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Abstract

Methods for the synthesis of amino(1,2,3-triazol-1-yl)-1,2,5-oxadiazoles (amino-triazolylfurazans) with CH2Cl and COCH2Br substituents in the triazole ring were developed and nucleophilic substitution for their halogen atom in reactions with N-, O-, and S-nucleophiles were studied. The possibility of displacing the NO2 group from the furazan and triazole rings in triazolylfurazans by an azido group was investigated. Novel compounds of this series were synthesized; the reaction rate and pathway were found to depend on the nature of the substrate and the reagent and the position of the substituent in isomers.

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References

  1. R. Bohm and Cr. Karov, Pharmazie, 1981, 4, 243.

    Google Scholar 

  2. I. A. Abdugafurov, N. Madikhanov, A. G. Makhsumov, Kh. M. Shakhidoyatov, A. A. Muzaffarov, A. U. Zokirov, and Sh. S. Masharipova, Azotistye geterotsikly i alkaloidy [Nitrogen Heterocycles and Alkaloids], Eds V. G. Kartsev and G. A. Tolstikov, Iridium-Press, Moscow, 2001, 2, 8 (in Russian).

    Google Scholar 

  3. V. G. Andrianov and A. V. Eremeev, Khim. Geterotsikl. Soedin., 1984, 1155 [Chem. Heterocycl. Compd., 1984 (Engl. Transl.)].

  4. P. Sauerberg, P. H. Olesen, S. Nielsen, S. Treppendahl, M. J. Sheardown, T. Honore, C. H. Mitch, J. S. Ward, A. J. Pike, F. P. Bymaster, B. D. Sawyer, and H. E. Shannon, J. Med. Chem., 1992, 35, 2274.

    Article  CAS  Google Scholar 

  5. A. B. Sheremetev, O. V. Kharitonova, E. V. Mantseva, V. O. Kulagina, E. V. Shatunova, N. S. Aleksandrova, T. M. Mel'nikova, E. A. Ivanova, D. E. Dmitriev, V. E. Eman, I. L. Yudin, V. S. Kuz'min, Yu. A. Strelenko, T. S. Novikova, O. V. Lebedev, and L. I. Khmel'nitskii, Zh. Org. Khim., 1999, 35, 1555 [Russ. J. Org. Chem., 1999, 35 (Engl. Transl.)].

    Google Scholar 

  6. A. B. Sheremetev, E. V. Mantseva, N. S. Aleksandrova, V. S. Kuz'min, and L. I. Khmel'nitskii, Mendeleev Commun., 1995, 25.

  7. L. I. Vereshchagin, L. G. Tikhonova, A. V. Maksikova, E. S. Serebryakova, A. G. Proidakov, and T. M. Fimennova, Zh. Org. Khim., 1980, 16, 730 [J. Org. Chem. USSR, 1980, 16 (Engl. Transl.)].

    CAS  Google Scholar 

  8. L. V. Batog, L. S. Konstantinova, V. Yu. Rozhkov, Yu. A. Strelenko, O. V. Lebedev, and L. I. Khmel'nitskii, Khim. Geterotsikl. Soedin., 2000, 100 [Chem. Heterocycl. Compd., 2000, 36, 91 (Engl. Transl.)].

    Google Scholar 

  9. L. V. Batog, V. Yu. Rozhkov, Yu. A. Strelenko, O. V. Lebedev, and L. I. Khmel'nitskii, Khim. Geterotsikl. Soedin., 2000, 406 [Chem. Heterocycl. Compd., 2000, 36, 343 (Engl. Transl.)].

    Google Scholar 

  10. L. V. Batog, V. Yu. Rozhkov, and M. I. Struchkova, Mendeleev Commun., 2002, 159.

  11. V. Yu. Rozhkov, L. V. Batog, E. K. Shevtsova, and M. I. Struchkova, Mendeleev Commun., 2004, 76.

  12. L. V. Batog, L. S. Konstantinova, and V. Yu. Rozhkov, Izv. Akad. Nauk, Ser. Khim., 2005, 1859 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1915].

    Google Scholar 

  13. P. H. Olesen, A. R. Sorensen, B. Urso, P. Kurtzhals, A. N. Bowler, U. Ehrbar, and B. F. Hansen, J. Med. Chem., 2003, 46, 3333.

    Article  CAS  Google Scholar 

  14. Weygand-Hilgetag, Organisch-chemische Experimentierkunst, Johann Ambrosius Barth Verlag, Leipzig, 1964, p. 942.

    Google Scholar 

  15. O. A. Rakitin, O. A. Zalesova, A. S. Kulikov, N. N. Makhova, T. I. Godovikova, and L. I. Khmel'nitskii, Izv. Akad. Nauk, Ser. Khim., 1993, 1949 [Russ. Chem. Bull., 1993, 42, 1865 (Engl. Transl.)].

  16. O. Dimroth, Liebigs Ann. Chem., 1909, 364, 183.

    CAS  Google Scholar 

  17. A. B. Sheremetev and O. V. Kharitonova, Mendeleev Commun., 1992, 157.

  18. M. A. Epishina, N. N. Makhova, L. V. Batog, L. S. Konstantinova, and L. I. Khmel'nitskii, Mendeleev Commun., 1994, 102.

  19. L. V. Batog, V. Yu. Rozhkov, L. S. Konstantinova, V. Yu. Eman, M. O. Dekaprilevich, Yu. T. Struchkov, S. E. Semenov, O. V. Lebedev, and L. I. Khmel'nitskii, Izv. Akad. Nauk, Ser. Khim., 1996, 1250 [Russ. Chem. Bull., 1996, 45, 1189 (Engl. Transl.)]; L. V. Batog, L. S. Konstantinova, O. V. Lebedev, and L. I. Khmel'nitskii, Mendeleev Commun., 1996, 193.

  20. N. K. Kochetkov, Zh. Obshch. Khim., 1955, 25, 1366 [J. Gen. Chem. USSR, 1955 (Engl. Transl.)].

    CAS  Google Scholar 

  21. A. B. Sheremetev, A. S. Kulikov, and L. I. Khmel'nitskii, Izv. Akad. Nauk, Ser. Khim., 1993, 744 [Russ. Chem. Bull., 1993, 42, 1189 (Engl. Transl.)].

    Google Scholar 

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1866–1876, August, 2005.

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Rozhkov, V.Y., Batog, L.V. & Struchkova, M.I. Nucleophilic substitution in the series of (1,2,3-triazol-1-yl)-1,2,5-oxadiazoles. Reactions with N-, O-, and S-nucleophiles. Russ Chem Bull 54, 1923–1934 (2005). https://doi.org/10.1007/s11172-006-0059-8

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  • DOI: https://doi.org/10.1007/s11172-006-0059-8

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