Skip to main content
SpringerLink
Log in

peri-Naphthylenediamines. 31. Study of interconversions of 2,3-dihydroperimidines and 1,8-bis(dialkylamino)naphthalenes. Convenient synthesis of 1,2,2,3-tetramethyl-2,3-dihydroperimidine and a monoisopropyl analog of the “proton sponge”

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Efficient procedures were developed for the two-step synthesis of 1,2,2,3-tetramethyl-2,3-dihydroperimidines and for the one-step synthesis of 1,3-dimethyl-2,3-dihydroperimidines starting from 1,8-diaminonaphthalenes. New possibilities of the use of 2,3-dihydroperimidinium salts in the synthesis of 1,8-bis(dialkylamino)naphthalenes (“proton sponges”) containing the N-isopropyl group along with the N-methyl groups were demonstrated. The 1,1,2,2,3-pentamethyl-2,3-dihydroperimidinium cation exists in the acyclic iminium form responsible for its high reactivity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. V. A. Ozeryanskii and A. F. Pozharskii, Izv. Akad. Nauk, Ser. Khim., 2000, 1412 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1406].

  2. N. V. Vistorobskii and A. F. Pozharskii, Zh. Org. Khim., 1989, 25, 2154 [Russ. J. Org. Chem., 1989, 25 (Engl. Transl.)].

    Google Scholar 

  3. L. Maresca, G. Natile, and F. P. Fanizzi, J. Chem. Soc., Dalton Trans., 1992, 11, 1867.

    Google Scholar 

  4. A. F. Pozharskii, Usp. Khim., 1998, 67, 3 [Russ. Chem. Rev., 1998, 67, 1 (Engl. Transl.)].

    Google Scholar 

  5. N. V. Vistorobskii, A. F. Pozharskii, S. V. Shorshnev, and A. I. Chernyshev, Mendeleev Commun., 1991, 10.

  6. A. F. Pozharskii, N. G. Tregub, N. V. Vistorobskii, E. Yu. Romanova, Z. A. Starikova, and A. I. Yanovskii, Izv. Akad. Nauk, Ser. Khim., 1999, 1311 [Russ. Chem. Bull., 1999, 48, 1299 (Engl. Transl.)].

    Google Scholar 

  7. A. F. Pozharskii, A. N. Suslov, and V. A. Kataev, Dokl. Akad. Nauk SSSR, 1977, 234, 841 [Dokl. Chem., 1977 (Engl. Transl.)].

    Google Scholar 

  8. A. A. Espenbetov, A. F. Pozharskii, Yu. T. Struchkov, and A. N. Suslov, Khim. Geterotsikl. Soedin., 1985, 977 [Chem. Heterocycl. Compd., 1985 (Engl. Transl.)].

  9. T. Barth and F. A. Neugebauer, J. Org. Chem., 1995, 60, 5401.

    Google Scholar 

  10. A. F. Pozharskii, L. P. Smirnova, A. I. Belyashova, N. N. Zatsepina, and I. F. Tupitsyn, Khim. Geterotsikl. Soedin., 1979, 961 [Chem. Heterocycl. Compd., 1979 (Engl. Transl.)].

  11. R. Gleiter and J. Uschmann, J. Org. Chem., 1986, 51, 370.

    Google Scholar 

  12. S. Bradbury, C. W. Rees, and R. C. Storr, J. Chem. Soc., Perkin Trans. 1, 1972, 68.

  13. A. F. Pozharskii and V. V. Dal'nikovskaya, Usp. Khim., 1981, 50, 1559 [Russ. Chem. Rev., 1981, 50 (Engl. Transl.)].

    Google Scholar 

  14. V. A. Ozeryanskii and A. F. Pozharskii, Izv. Akad. Nauk, Ser. Khim., 2000, 1405 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1399].

  15. A. G. Giumanini, G. Chiavari, M. M. Musiani, and P. Rossi, Synthesis, 1980, 743.

  16. A. F. Pozharskii and I. S. Kashparov, Khim. Geterotsikl. Soedin., 1972, 860 [Chem. Heterocycl. Compd., 1972 (Engl. Transl.)].

  17. V. I. Sokolov, A. F. Pozharskii, I. S. Kashparov, A. G. Ivanov, and B. I. Ardashev, Khim. Geterotsikl. Soedin., 1974, 558 [Chem. Heterocycl. Compd., 1974 (Engl. Transl.)].

  18. A. F. Pozharskii, L. A. Kurasov, V. V. Kuz'menko, and L. L. Popova, Zh. Org. Khim., 1981, 17, 1005 [J. Org. Chem. USSR, 1981, 17 (Engl. Transl.)].

    Google Scholar 

  19. R. W. Alder, M. R. Bryce, N. C. Goode, N. Miller, and J. Owen, J. Chem. Soc., Perkin Trans. 1, 1981, 2840.

  20. A. F. Pozharskii, V. A. Ozeryanskii, and V. V. Kuz'menko, Zh. Org. Khim., 1996, 32, 76 [Russ. J. Org. Chem., 1996, 32 (Engl. Transl.)].

    Google Scholar 

  21. A. F. Pozharskii, E. A. Filatova, N. V. Vistorobskii, and I. V. Borovlev, Khim. Geterotsikl. Soedin., 1999, 365 [Chem. Heterocycl. Compd., 1999 (Engl. Transl.)].

  22. A. F. Pozharskii, A. N. Suslov, N. M. Starshikov, L. L. Popova, N. A. Klyuev, and V. A. Adanin, Zh. Org. Khim., 1980, 16, 2216 [J. Org. Chem. USSR, 1980, 16 (Engl. Transl.)].

    Google Scholar 

  23. R. W. Alder and J. E. Anderson, J. Chem. Soc., Perkin Trans. 2, 1973, 2086.

  24. V. A. Ozeryanskii and A. F. Pozharskii, Izv. Akad. Nauk, Ser. Khim., 1997, 1501 [Russ. Chem. Bull., 1997, 46, 1437 (Engl. Transl.)].

  25. J. S. Whitehurst, J. Chem. Soc., 1951, 215.

  26. F. Sachs, Justus Liebigs Ann. Chem., 1909, 365, 53.

    Google Scholar 

  27. A. J. Gordon and R. A. Ford, The Chemist's Companion, the Handbook of Practical Data, Techniques, and References, J. Wiley, New York-London-Sydney-Toronto, 1972.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Rostov State University, 7 ul. Zorge, 344090, Rostov-on-Don, Russian Federation

    V. A. Ozeryanskii, E. A. Filatova, V. I. Sorokin & A. F. Pozharskii

Authors
  1. V. A. Ozeryanskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. A. Filatova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. I. Sorokin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. F. Pozharskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ozeryanskii, V.A., Filatova, E.A., Sorokin, V.I. et al. peri-Naphthylenediamines. 31. Study of interconversions of 2,3-dihydroperimidines and 1,8-bis(dialkylamino)naphthalenes. Convenient synthesis of 1,2,2,3-tetramethyl-2,3-dihydroperimidine and a monoisopropyl analog of the “proton sponge”. Russian Chemical Bulletin 50, 846–853 (2001). https://doi.org/10.1023/A:1011359109826

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1011359109826

Search

Navigation