Skip to main content
Log in

Cyclization ofN-acetyl-ortho-cycloalkenylanilines on treatment with bromine andN-bromosuccinimide

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The reaction ofN-acetyl-2-(cyclohex-1-enyl)aniline with Br2 orN-bromsuccinimide at 20°C is accompanied by intramolecular cyclization to give brominated 3,1-benzoxazines or 4-acetyl-(3-bromo-5-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. R. R. Gataullin, I. S. Afon'kin, I. V. Pavlova, and I. B. Abdrakhmanov,Izv. Akad. Nauk, Ser. Khim., 1999, 398 [Russ. Chem. Bull. 1999,48, 396 (Engl. Transl.)].

    Google Scholar 

  2. R. R. Gataullin, T. V. Kazhanova, L. T. Il'yasova, A. A. Fatykhov, L. V. Spirikhin, and I. B. Abdrakhmanov,Izv. Akad. Nauk, Ser. Khim., 1999, 975 [Russ. Chem. Bull., 1999,48, 967 (Engl. Transl.)].

    Google Scholar 

  3. C. Cardillo and M. Orena,Tetrahedron, 1990,46, 3321.

    Article  CAS  Google Scholar 

  4. I. B. Abdrakhmanov, V. M. Sharafutdinov, and G. A. Tolstikov,Izv. Akad. Nauk SSSR, Ser. Khim., 1982, 2160 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1982,31 (Engl. Transl.)].

    Google Scholar 

  5. S. Knapp, M. J. Sebastian, and H. Ramanathan,J. Org. Chem., 1983,48, 4786.

    Article  CAS  Google Scholar 

  6. E. J. Corey, M. Shibasaki, and J. Knolle,Tetrohedron Lett., 1977,16, 1625.

    Article  Google Scholar 

  7. M. Georges and B. Fraser-Reid,J. Am. Chem. Soc., 1980,102, 3956.

    Article  Google Scholar 

  8. B. I. Ionin, B. A. Ershov, and A. I. Kol'tsov,YaMR-spektroskopiya v organicheskoi khimii [NMR Spectroscopy in Organic Chemistry], Nauka, Leningrad, 1983, 170 (in Russian).

    Google Scholar 

  9. I. A. Korbukh, L. N. Abramova, and M. N. Preobrazhenskaya,Zh. Org. Khim., 1977,13, 731 [J. Org. Chem. USSR, 1977,13 (Engl. Transl.)].

    CAS  Google Scholar 

  10. A. G. Mustafin, M. A. Petrova, R. R. Gataullin, L. V. Spirikhin, A. A. Fatykhov, I. B. Abdrakhmanov, L. F. Chertanova, and G. A. Tolstikov,Izv. Akad. Nauk, Ser. Khim., 1998, 1378 [Russ. Chem. Bull., 1998,47, 1340 (Engl. Transl.)].

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 118–120, January, 2000.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gataullin, R.R., Afon'kin, I.S., Fatykhov, A.A. et al. Cyclization ofN-acetyl-ortho-cycloalkenylanilines on treatment with bromine andN-bromosuccinimide. Russ Chem Bull 49, 122–124 (2000). https://doi.org/10.1007/BF02499076

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02499076

Key words

Navigation