Skip to main content
SpringerLink
Log in

[3+2] Cycloaddition of Dimethyl Acetylenedicarboxylate, Methyl Acrylate, and Ethyl Acrylate to 4,5-Dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1'-cyclohexane] N-Oxide

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The cycloaddition of methyl acrylate and ethyl acrylate to 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1'-cyclohexane] N-oxide proceeds without either regiospecificity or stereospecificity. Eight geometrical isomers of spiro[isoxazolidino[3,2-a]benz-2-azepine-5,1'-cyclohexane] were formed, of which several were isolated as pure samples. The cycloaddition of dimethyl acetylenedicarboxylate proceeds stereoselectively, leading to spiro[isoxazolino[3,2-a]benz-2-azepine-5,1'-cyclohexane] with cis arrangement of the protons at C(7) and C(11b).

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.

Similar content being viewed by others

REFERENCES

  1. A. Varlamov, V. Kouznetsov, F. Zubkov, A. Chernyshev, G. Alexandrov, A. Palma, L. Vargas, and S. Salas, Synthesis, 849 (2001).

  2. V. Kouznetsov, A. R. Palma, S. Salas, L. Y. Vargas, F. I. Zubkov, A. V. Varlamov, and J. R. Martinez, J. Heterocycl. Chem., 34, 1591 (1997).

    Google Scholar 

  3. A. V. Varlamov, F. I. Zubkov, K. F. Turchin, A. I. Chernyshev, and R. S. Borisov, Khim. Geterotsikl. Soedin., 1360 (2001).

  4. A. V. Varlamov, K. F. Turchin, A. I. Chernyshev, F. I. Zubkov, and T. N. Borisova, Khim. Geterotsikl. Soedin., 703 (2000).

  5. A. V. Varlamov, F. I. Zubkov, K. F. Turchin, A. I. Chernyshev, and A. N. Levov, Khim. Geterotsikl. Soedin., 1144 (2000).

  6. V. V. Kuznetsov, S. V. Lantsetov, A. E. Aliev, A. V. Varlamov, and N. S. Prostakov, Zh. Org. Khim., 28, 74 (1992).

    Google Scholar 

  7. P. N. Confalone and E. M. Huie, Organic Reactions, 36, 1 (1988).

    Google Scholar 

  8. J.-G. Shvekhgeimer, Khim. Geterotsikl. Soedin., 435 (1998).

Download references

Author information

Authors and Affiliations

  1. Russian People's Friendship University, 117198, Moscow

    A. V. Varlamov, A. I. Chernyshev, F. I. Zubkov & A. N. Levov

  2. Pharmaceutical Chemical Center, All-Russian Pharmaceutical Chemistry Institute, 119815, Moscow

    K. F. Turchin

Authors
  1. A. V. Varlamov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. I. Chernyshev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. F. I. Zubkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. K. F. Turchin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. N. Levov
    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

Varlamov, A.V., Chernyshev, A.I., Zubkov, F.I. et al. [3+2] Cycloaddition of Dimethyl Acetylenedicarboxylate, Methyl Acrylate, and Ethyl Acrylate to 4,5-Dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1'-cyclohexane] N-Oxide. Chemistry of Heterocyclic Compounds 40, 364–369 (2004). https://doi.org/10.1023/B:COHC.0000028634.08685.99

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:COHC.0000028634.08685.99

Search

Navigation