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Alkylation of 1-alkoxy-3-methyl-1-triazene 2-oxide sodium salts

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Abstract

1-Alkoxy-3-methyl-1-triazene 2-oxide sodium salts react with chloromethyl methyl sulfide to give a mixture of 1-alkoxy-3-methyl-3-(methylthiomethyl)-1-triazene 2-oxides and 3-alkoxy-1-methyl-3-(methylthiomethyl)-1-triazene 2-oxides. The reaction of these triazene oxide sodium salts with 3,3-dialkyl-1-chloromethoxy-1-triazene 2-oxides produces a complex mixture of product bearing the oxytriazene moieties of the starting alkoxy-1-triazene 2-oxides bonded with the methylene group as a key structural fragment.

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References

  1. V. G. Granik, N. B. Grigorév, Oksid azota (NO) [Nitric oxide (NO)], Vyzovskaya kniga, Moscow, 2004, 359 pp. (in Russian).

    Google Scholar 

  2. V. P. Ananikov, E. A. Khokhlova, M. P. Egorov, A. M. Sakharov, S. G. Zlotin, A. V. Kucherov, L. M. Kustov, M. L. Gening, N. E. Nifantiev, Mendeleev Commun., 2015, 25, 75.

    Article  CAS  Google Scholar 

  3. L. L. Fershtat, M. A. Epishina, A. S. Kulikov, M. I. Struchkova, N. N. Makhova, Chem. Heterocycl. Compd., 2015, 51, 176.

    Article  CAS  Google Scholar 

  4. L. Fershtat, I. Ananyev, N. Makhova, RSC Adv., 2015, 5, 47248.

    Article  CAS  Google Scholar 

  5. M. A. Bastrakov, A. M. Starosotnikov, V. V. Kachala, I. L. Dalinger, S. A. Shevelev, Chem. Heterocycl. Compd. (Engl. Transl.), 2015, 51, 496 [Khim. Geterotsikl. Soedin., 2015, 51, 496].

    Article  CAS  Google Scholar 

  6. A. A. Voronin, V. P. Zelenov, A. M. Churakov, Yu. A. Strelenko, V. A. Tartakovskii, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 699 [Izv. Akad. Nauk, Ser. Khim., 2015, 699].

    Article  CAS  Google Scholar 

  7. Yu. P. Artsybasheva, B. V. Ioffe, J. Org. Chem. USSR (Engl. Transl.), 1987, 23, 1056 [Zh. Org. Khim., 1987, 23, 1168].

    Google Scholar 

  8. R. S. Nandurdikar, L. K. Keefer, A. E. Maciag, Z. Cao, J. E. Saavedra, Bioorg. Med. Chem., 2012, 20, 2025.

    Article  CAS  Google Scholar 

  9. J. Kaur, A. Bhardwaj, Z. Haung, E. E. Knaus, D. Narang, T.-Y. Chen, F. Plane, J. Med. Chem., 2012, 55, 7883.

    Article  CAS  Google Scholar 

  10. US Pat. W02009/94242 A1, 2009.

  11. G. A. Smirnov, P. B. Gordeev, S. V. Nikitin, G. V. Pokhvisneva, T. V. Ternikova, O. A. Lukýanov, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 1057 [Izv. Akad. Nauk, Ser. Khim., 2015, 1057].

    Article  CAS  Google Scholar 

  12. G. A. Smirnov, S. V. Nikitin, P. B. Gordeev, G. V. Pokhvisneva, T. V. Ternikova, O. A. Lukýanov, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 2706 [Izv. Akad. Nauk, Ser. Khim., 2015, 2706].

    Google Scholar 

  13. G. A. Smirnov, P. B. Gordeev, S. V. Nikitin, G. V. Pokhvisneva, T. V. Ternikova, O. A. Lukýanov, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 2712 [Izv. Akad. Nauk, Ser. Khim., 2015, 2712].

    Google Scholar 

  14. O. A. Lukýanov, G. V. Pokhvisneva, T. V. Ternikova, G. A. Smirnov, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 1062 [Izv. Akad. Nauk, Ser. Khim., 2015, 1062].

    Article  Google Scholar 

  15. J. E. Saavedra, D. S. Bohle, K. N. Smith, C. George, J. R. Deschamps, D. Parrish, J. Ivanic, Y.-N. Wang, M. L. Citro, L. K. Keefer, J. Am. Chem. Soc., 2004, 126, 12880.

    Article  CAS  Google Scholar 

  16. R. S. Nandurdikar, L. K. Keefer, J. E. Saavedra, Chem. Commun., 2011, 47, 6710.

    Article  CAS  Google Scholar 

  17. D. Scott Bohle, L. K. Keefer, J. E. Saavedra, Tetrahedron Lett., 2009, 50, 5917.

    Article  Google Scholar 

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Correspondence to G. A. Smirnov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2851—2856, December, 2015.

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Smirnov, G.A., Gordeev, P.B., Nikitin, S.V. et al. Alkylation of 1-alkoxy-3-methyl-1-triazene 2-oxide sodium salts. Russ Chem Bull 64, 2851–2856 (2015). https://doi.org/10.1007/s11172-015-1237-3

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  • DOI: https://doi.org/10.1007/s11172-015-1237-3

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