Skip to main content
SpringerLink
Log in

4H-3,1-benzoxazines from benzyl cyclopropanes. First example of acid catalyzed rearrangement in ortho-substituted benzylcyclo-propanes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The synthesis of 2-N-acylamino-substituted benzylcyclopropanes has been carried out. It was established that under the action of acids 2-N-acylamino-substituted benzylcyclopropanes are rearranged into the corresponding 4H-3,1-benzoxazines and not into the expected 3,1-benzoxazepines. It was shown that a similar type of rearrangement is also characteristic for 2-N-acylamino-substituted allylbenzenes.

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. Yu. S. Shabarov, S. S. Mochalov, and I. P. Stepanova, Dokl. Akad. Nauk SSSR, 189, 1028 (1969).

    CAS  Google Scholar 

  2. T. G. Kutateladze, A. N. Fedotov, S. S. Mochalov, and Yu. S. Shabarov, USSR Authors' Certificate, 1502570; Byul. Izobret., No. 31, 134 (1989).

    Google Scholar 

  3. S. S. Mochalov, R. A. Gazzaeva, A. N. Fedotov, Yu. S. Shabarov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 922 (2003). [Chem. Heterocycl. Comp., 39, 794 (2003)].

    Google Scholar 

  4. T. G. Kutateladze, I. N. Shishkina, A. N. Fedotov, S. S. Mochalov, and Yu. S. Shabarov, USSR Authors' Certificate 1268578; Byul. Izobret., No. 41, 98 (1986).

  5. A. N. Fedotov, I. N. Shishkina, T. G. Kutateladze, S. S. Mochalov, and Yu. S. Shabarov, Khim. Geterotsikl. Soedin., 1063 (1987). [Chem. Heterocycl. Comp., 23, 849 (1987)].

    Google Scholar 

  6. T. G. Kutateladze, E. V. Trofimova, A. N. Fedotov, S. S. Mochalov, and Yu. S. Shabarov, USSR Authors' Certificate 1432977; Byul. Izobret., No. 39, 290 (1988).

    Google Scholar 

  7. T. G. Kutateladze, A. N. Fedotov, S. S. Mochalov, and Yu. S. Shabarov, USSR Authors' Certificate 1397436; Byul. Izobret., No. 19, 96 (1988).

    Google Scholar 

  8. T. G. Kutateladze, A. N. Fedotov, S. S. Mochalov, and Yu. S. Shabarov, USSR Authors' Certificate 1493641; Byul. Izobret., No. 26, 118 (1989).

    Google Scholar 

  9. S. S. Mochalov, D. V. Kosynkin, I. D. Yudin, K. A. Zavodskikh, Yu. S. Shabarov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 472 (1994). [Chem. Heterocycl. Comp., 30, 413 (1994)].

    Google Scholar 

  10. S. S. Mochalov, A. N. Fedotov, T. G. Kutateladze, E. V. Trofimova, Yu. S. Shabarov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 321 (1998). [Chem. Heterocycl. Comp., 34, 288 (1998)].

    Google Scholar 

  11. E. V. Trofimova, A. N. Fedotov, S. S. Mochalov, Yu. S. Shabarov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 1385 (2000). [Chem. Heterocycl. Comp., 36, 1198 (2000)].

    Google Scholar 

  12. A. N. Fedotov, E. V. Trofimova, V. A. Sidorov, K. A. Potekhin, V. A. Romanov, S. S. Mochalov, and N. S. Zefirov, Dokl. Akad. Nauk Ross., 405, 65 (2005).

    Google Scholar 

  13. A. N. Fedotov, E. V. Trofimova, V. A. Romanov, S. S. Mochalov, Yu. S. Shabarov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 115 (2008). [Chem. Heterocycl. Comp., 44, 96 (2008)].

    Google Scholar 

  14. S. S. Mochalov, T. G. Kutateladze, A. N. Fedotov, and Yu. S. Shabarov, Dokl. Akad. Nauk SSSR, 298, 1398 (1988).

    CAS  Google Scholar 

  15. A. N. Fedotov, E. V. Trofimova, S. S. Mochalov, and Yu. S. Shabarov, Zh. Org. Khim., 24, 1413 (1988).

    CAS  Google Scholar 

  16. A. N. Fedotov, E. V. Trofimova, S. S. Mochalov, and Yu. S. Shabarov, Zh. Org. Khim., 24, 2403 (1988).

    CAS  Google Scholar 

  17. S. S. Mochalov, E. V. Trofimova, A. N. Fedotov, Yu. S. Shabarov, and N. S. Zefirov, Zh. Org. Khim., 32, 852 (1996).

    CAS  Google Scholar 

  18. S. S. Mochalov, A. N. Fedotov, R. A. Gazzaeva, B. P. Archegov, E. V. Trofimova, and N. S. Zefirov, Zh. Org. Khim., 37, 935 (2001).

    Google Scholar 

  19. E. V. Trofimova, A. N. Fedotov, R. A. Gazzaeva, S. S. Mochalov, Yu. S. Shabarov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 234 (2003). [Chem. Heterocycl. Comp., 39, 205 (2003)].

    Google Scholar 

  20. S. S. Mochalov, A. N. Fedotov, A. A. Borisenko, V. V. Tkachev, G. V. Shilov, A. I. Utenyshev, M. A. Aldoshin, and N. S. Zefirov, Dokl. Akad. Nauk Ross., 391, 646 (2003).

    Google Scholar 

  21. R. A. Gazzaeva, S. S. Mochalov, B. P. Archegov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 302 (2005). [Chem. Heterocycl. Comp., 41, 272 (2005)].

    Google Scholar 

  22. S. S. Mochalov, Ya. I. Kuz'min, A. N. Fedotov, E. V. Trofimova, R. A. Gazzaeva, Yu. S. Shabarov, and N. S. Zefirov, Zh. Org. Khim., 34, 1379 (1998).

    Google Scholar 

  23. R. A. Gazzaeva, B. P. Archegov, A. N. Fedotov, E. V. Trofimova, S. S. Mochalov, and Yu. S. Shabarov, Vestn. Mosk. Gos. Univ., Ser. 2, Khim., 46, 349 (2005).

    CAS  Google Scholar 

  24. R. A. Gazzaeva, M. I. Khasanov, S. S. Mochalov, and N. S. Zefirov, Khim. Geterotsikl. Soedin., 941 (2007). [Chem. Heterocycl. Comp., 43, 799 (2007)].

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Moscow M. V. Lomonosov State University, Moscow, 119992, Russia

    E. V. Trofimova, B. P. Archegov, A. N. Fedotov, R. A. Gazzaeva, S. S. Mochalov & N. S. Zefirov

Authors
  1. E. V. Trofimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. B. P. Archegov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. N. Fedotov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. A. Gazzaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. S. Mochalov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. N. S. Zefirov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. N. Fedotov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1368-1379, September, 2009.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Trofimova, E.V., Archegov, B.P., Fedotov, A.N. et al. 4H-3,1-benzoxazines from benzyl cyclopropanes. First example of acid catalyzed rearrangement in ortho-substituted benzylcyclo-propanes. Chem Heterocycl Comp 45, 1095–1104 (2009). https://doi.org/10.1007/s10593-009-0400-x

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-009-0400-x

Keywords

Search

Navigation