Skip to main content
SpringerLink
Log in

Synthesis and molecular structure of 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives and dimethyl 4-cyano-2,3,6,7-tetrahydro-1H-3-benzazonine-5,6-dicarboxylate

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A study was carried out on the direction of 1,2,3,4-tetrahydroisoquinolinium quaternary salt rearrangements by the action of base with or without dimethyl acetylenedicarboxylate. These quaternary salts containing a methylene group at the nitrogen atom, are converted in the presence of base through intermediate N-ylides into the Stevens rearrangement products, namely, tetrahydro-3-benzazepines. Upon the addition of dimethyl acetylenedicarboxylate as an electrophilic trap, this diester adds at the carbanion site of the ylide with subsequent recyclization of the piperidine fragment to give a 2-benzazonine derivative with an unusual 4,5-positioning of the olefin bond in the nine-membered heterocycle. An X-ray structural analysis established the molecular structures of 2-cyano-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and dimethyl 4-cyano-2,3,6,7-tetrahydro-1H-3-benzazo-nine-5,6-dicarboxylate.

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

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. T. Ye and A. M. McKervey, Chem. Rev., 94, 1901 (1994).

    Article  Google Scholar 

  2. N. Isono and M. Mori, J. Org. Chem., 60, 1480 (1995).

    Article  Google Scholar 

  3. J. A. Vanecko, H. Wan, and F. G. West, Tetrahedron, 62, 1043 (2006).

    Article  CAS  Google Scholar 

  4. S. Chumpradit, H. F. Kung, J. Billings, M. P. Kung, and S. Pan, J. Med. Chem., 32, 1431 (1989).

    Article  CAS  Google Scholar 

  5. J. L. Neumeyr, N. S. Kula, R. J. Baldessarini, and N. Baidur, J. Med. Chem., 35, 1466 (1992).

    Article  Google Scholar 

  6. T. Kametani and K. Fukumoto, Heterocycles, 3, 931 (1975).

    Article  CAS  Google Scholar 

  7. B. Renfroe, C. Harrington, and G. R. Proctor, in: A. Rosowsky (editor), Heterocyclic Compounds. Azepines, Part I, Wiley, New York (1984).

    Google Scholar 

  8. T. Hudlicky, L. D. Kwart, and J. W. Reed, in: S. W. Pelleter (editor), Alkaloids: Chemical and Biological Perspectives, Vol. 5, Springer Verlag, New York (1987).

    Google Scholar 

  9. D. C. Znou, R. Zittoun, and J. P. Marie, Bull. Cancer, 82, 987 (1995).

    Google Scholar 

  10. A. T. Soldatenkov, S. V. Volkov, and S. A. Soldatova, Khim. Geterotsikl. Soedin., 613 (2007). [Chem. Heterocycl. Compd., 43, 508 (2007)].

    Google Scholar 

  11. G. S. Gimranova, S. A. Soldatova, E. G. Prokudina, A. T. Soldatenkov, and K. B. Polyanskii, Zh. Org. Khim., 44, 1416 (2008). [Russ. J. Org. Chem., 44, 1399 (2008)].

    Google Scholar 

  12. N. S. Prostakov, A. T. Soldatenkov, P. K. Radzhan, and M. V. Bagdadi, Khim. Geterotsikl. Soedin., 706 (1982). [Chem. Heterocycl. Compd., 18, 542 (1982)].

    Google Scholar 

  13. N. S. Prostakov, A. T. Soldatenkov, P. K. Radzhan, A. Samal’oa, V. F. Zakharov, and V. P. Zvolinskii, Khim. Geterotsikl. Soedin., 252 (1983). [Chem. Heterocycl. Compd., 19, 206 (1983)].

    Google Scholar 

  14. S. A. Soldatova, S. V. Akbulatov, G. S. Gimranova, Yu. O. Rudakov, K. B. Polyanskii, and A. T. Soldatenkov, Khim. Geterotsikl. Soedin., 789 (2005). [Chem. Heterocycl. Compd., 41, 681 (2005)].

    Google Scholar 

  15. S. A. Soldatova, G. S. Gimranova, J. A. Mamyrbekova, K. B. Polyanskii, S. V. Akbulatov, and A. T. Soldatenkov, Khim. Geterotsikl. Soedin., 1670 (2007). [Chem. Heterocycl. Compd., 43, 1420 (2007)].

    Google Scholar 

  16. G. S. Gimranova, S. A. Soldatova, A. T. Soldatenkov, and K. B. Polyanskii, Zh. Org. Khim., 44, 758 (2008). [Russ. J. Org. Chem., 44, 750 (2008)].

    Google Scholar 

  17. A. T. Soldatenkov, S. A. Soldatova, R. R. Suleimanov, N. M. Kolyadina, and V. N. Khrustalev, Khim. Geterotsikl. Soedin., 306 (2010). [Chem. Heterocycl. Compd., 46, 245 (2010)].

    Google Scholar 

  18. A. T. Soldatenkov, S. A. Soldatova, A. V. Malkova, N. M. Kolyadina, and V. N. Khrustalev, Khim. Geterotsikl. Soedin., 1751 (2009). [Chem. Heterocycl. Compd., 45, 1410 (2009)].

    Google Scholar 

  19. L. F. Tietze and T. Eicher, Preparative Organic Chemistry [Russian translation], Mir, Moscow (1999), p. 549.

    Google Scholar 

  20. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).

Download references

Author information

Authors and Affiliations

  1. Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    A. T. Soldatenkov, S. A. Soldatova, G. S. Gimranova, A. V. Malkova, K. B. Polyanskii & N. M. Kolyadina

  2. University of Abobo-Ajamé, 02 BP801, Abidjan, Republic of Côte d’Ivoire

    J. A. Mamyrbekova-Bekro

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 117813, Russia

    V. N. Khrustalev

Authors
  1. A. T. Soldatenkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. A. Soldatova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. J. A. Mamyrbekova-Bekro
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. S. Gimranova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. V. Malkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. K. B. Polyanskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. N. M. Kolyadina
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. V. N. Khrustalev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. A. Soldatova.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1430-1437, September, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Soldatenkov, A.T., Soldatova, S.A., Mamyrbekova-Bekro, J.A. et al. Synthesis and molecular structure of 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives and dimethyl 4-cyano-2,3,6,7-tetrahydro-1H-3-benzazonine-5,6-dicarboxylate. Chem Heterocycl Comp 48, 1332–1339 (2012). https://doi.org/10.1007/s10593-012-1141-9

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-1141-9

Keywords

Search

Navigation