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Regioselective Alkylation of 5-Substituted Tetrazoles with 3-Chlorobut-2-en-1-ol in Acid Medium

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Abstract

The alkylation of 5-R-tetrazoles (R = H, Me, Ph) with 3-chlorobut-2-en-1-ol was studied in 1,2-dichloroethane, chlorofom, and methylene chloride in the presence of boron trifluoride—diethyl ether complex, as well as in trifluoroacetic acid and in ethyl acetate in the presence of sulfuric acid. The reaction in 1,2-dichloroethane catalyzed by BF3 · Et2O gave 70–80% of the alkylation products containing no less than 99% of the 2-substituted isomer.

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References

  1. Ostrovskii, VA., Trifonov, R.E., and Popova, E.A., Russ. Chem. Bull., Int. Ed., 2012, vol. 61, p. 768. doi https://doi.org/10.1007/s11172-012-0108-4

    Article  CAS  Google Scholar 

  2. Kozyro, A.A., Simirskii, V.V., Krasulin, A.P., Sevruk, V.M., Kabo, G.Ya., Frenkel’, M.L., Gaponik, P.N., and Grigor’ev, Yu.V, Zh. Fiz. Khim., 1990, vol. 64, p. 656.

    CAS  Google Scholar 

  3. Koldobskii, G.I. and Ostrovskii, VA., Russ. Chem. Rev., 1994, vol. 63, p. 797. doi https://doi.org/10.1070/RC1994v063n10ABEH000119

    Article  Google Scholar 

  4. Ostrovskii, V.A. and Koren’, A.O., Heterocycles, 2000, vol. 53, p. 1421. doi https://doi.org/10.3987/REV-00-530

    Article  CAS  Google Scholar 

  5. Koren’, A.O. and Gaponik, P.N., Chem. Heterocycl. Compd., 1990, vol. 26, p. 1366. doi https://doi.org/10.1007/BF00473965

    Article  Google Scholar 

  6. Koren’, A.O., Gaponik, P.N., and Ostrovskii, V.A., Int. J. Chem. Kinet., 1993, vol. 25, p. 1043. doi https://doi.org/10.1002/kin.550251209

    Article  Google Scholar 

  7. Koren’, A.O. and Gaponik, P.N., Chem. Heterocycl. Compd., 1991, vol. 27, p. 1036. doi https://doi.org/10.1007/BF00484379

    Article  Google Scholar 

  8. Gaponik, P.N. Voiketovich, S.V., and Klyaus, B.G., Russ. J. Org. Chem., 2004, vol. 40, p. 598. doi https://doi.org/10.1023/B:RUJO.0000036092.15897.ba

    Article  CAS  Google Scholar 

  9. Koren’, A.O., Gaponik, P.N., and Ostrovskii, V.A., Int. J. Chem. Kinet., 1995, vol. 27, p. 919. doi https://doi.org/10.1002/kin.550270908

    Article  Google Scholar 

  10. Lisakova, A.D., Ryabukhin, D.S., Trifonov, R.E., Ostrovskii, V.A., and Vasilyev, A.V., Tetrahedron Lett., 2015, vol. 56, p. 7020. doi https://doi.org/10.1016/j.tetlet.2015.11.005

    Article  CAS  Google Scholar 

  11. Voitekhovich, S.V., Gaponk, P.N., and Koren, A.O., Mendeleev Commun., 1997, vol. 7, no. 1, p. 41. doi https://doi.org/10.1070/MC1997v007n01ABEH000654

    Article  Google Scholar 

  12. Rabinovich, V.A., Kratkii khimicheskii spravochnik (Brief Chemical Reference Book), Moscow: Khimiya, 1977.

    Google Scholar 

Download references

Acknowledgments

This study was performed using the facilities of the Engineering Center of the St. Petersburg State Institute of Technology.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    S. A. Egorov, M. A. Ishchenko, N. A. Kirilov & R. S. Iskhakov

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  1. S. A. Egorov
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  2. M. A. Ishchenko
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  3. N. A. Kirilov
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  4. R. S. Iskhakov
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Correspondence to S. A. Egorov.

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The authors declare the absence of conflict of interests.

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Egorov, S.A., Ishchenko, M.A., Kirilov, N.A. et al. Regioselective Alkylation of 5-Substituted Tetrazoles with 3-Chlorobut-2-en-1-ol in Acid Medium. Russ J Org Chem 55, 525–529 (2019). https://doi.org/10.1134/S1070428019040183

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  • DOI: https://doi.org/10.1134/S1070428019040183

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