Skip to main content
SpringerLink
Log in

Acylation reaction of the 3,3-dimethylisoquinoline series enaminonitrile and properties of 5,5-dimethyl- 2,3-dioxo-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline- 1-carbonitrile

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

2-(3,3-Dimethyl-3,4-dihydro-2H-isoquinolin-1-ylidene)acetonitrile containing an enamine fragment has been acylated using acetyl or benzoyl chlorides to give the corresponding enamino ketones. The acylation using oxalyl chloride gives 5,5-dimethyl-2,3-dioxo-2,3,5,6-tetrahydropyrrolo[2,1-a]-isoquinoline-1-carbonitrile. Reaction of the latter with guanidine carbonate or o-phenylenediamine is accompanied by opening of the pyrrole ring and heterocyclization to give the corresponding 2-amino-4-imidazolone and 2-quinoxalone derivatives. Linear amines were formed in similar reactions with m-toluidine, 1-aminoadamantane, o-aminophenol, and 2-amino-3-hydroxypyridine.

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. A. G. Mikhailovskii and M. I. Vakhrin, Khim. Geterotsikl. Soedin., 227 (2002). [Chem. Heterocycl. Compd., 38, 205 (2002)].

    Google Scholar 

  2. V. A. Glushkov, V. I. Karmanov, and Yu. V. Shklyaev, Khim. Geterotsikl. Soedin., 558 (2005). [Chem. Heterocycl. Compd., 41, 475 (2005)].

    Google Scholar 

  3. V. S. Shklyaev, B. B. Aleksandrov, A. G. Mikhailovskii, and M. I. Vakhrin, Khim. Geterotsikl. Soedin., 963 (1987). [Chem. Heterocycl. Compd., 23, 790 (1987)].

    Google Scholar 

  4. A. G. Mikhailovskii and V. S. Shklyaev, Khim. Geterotsikl. Soedin., 946 (1994). [Chem. Heterocycl. Compd., 30, 818 (1994)].

    Google Scholar 

  5. A. G. Mikhailovskii and V. S. Shklyaev, Khim. Geterotsikl. Soedin., 291 (1997). [Chem. Heterocycl. Compd., 33, 243 (1997)].

    Google Scholar 

  6. A. G. Mikhailovskii, N. N. Polygalova, T. S. Turova, G. A. Lobashova, and M. I. Vakhrin, Khim. Geterotsikl. Soedin., 1357 (2004). [Chem. Heterocycl. Compd., 40, 1174 (2004)].

    Google Scholar 

  7. N. N. Polygalova and A. G. Mikhailovskii, Khim. Geterotsikl. Soedin., 1378 (2005). [Chem. Heterocycl. Compd., 41, 1173 (2005)].

    Google Scholar 

  8. N. N. Polygalova and A. G. Mikhailovskii, Khim. Geterotsikl. Soedin., 1383 (2005). [Chem. Heterocycl. Compd., 41, 1178 (2005)].

    Google Scholar 

  9. O. V. Surikova, A. G. Mikhailovskii, and M. I. Vakhrin, Khim. Geterotsikl. Soedin., 298 (2008). [Chem. Heterocycl. Compd., 44, 231 (2008)].

    Google Scholar 

  10. O. V. Surikova, A. G. Mikhailovskii, N. N. Polygalova, and M. I. Vakhrin, Zh. Org. Khim., 43, 852 (2008).

    Google Scholar 

  11. O. V. Surikova, Z. G. Aliev, A. G. Mikhailovskii, N. N. Polygalova, and M. I. Vakhrin, Zh. Org. Khim., 44, 909 (2008).

    Google Scholar 

  12. O. V. Surikova, A. G. Mikhailovskii, N. N. Polygalova, P. G. Neifel’d, and M. I. Vakhrin, Zh. Org. Khim., 44, 1416 (2008).

    Google Scholar 

  13. O. V. Surikova, A. G. Mikhailovskii, and M. I. Vakhrin, Khim. Geterotsikl. Soedin., 1412 (2009). [Chem. Heterocycl. Compd., 45, 1131 (2009)].

    Google Scholar 

  14. A. J. Gordon and R. A. Ford, A Chemists Companion [Russian translation], Mir, Moscow (1976), p. 285.

    Google Scholar 

  15. E. Pretsch, P. Bühlmann, and C. Affolter, Structural Determination of Organic Compounds [Russian translation], Mir, Moscow (2006), p. 183.

    Google Scholar 

  16. T. Sano, Y. Horiguchi, and Y. Tsuda, Heterocycles, 3, 65 (1975).

    Article  Google Scholar 

  17. Y. Tsuda, M. Kaneda, Y. Itatani, T. Sano, H. Horiguchi, and Y. Iitaka, Heterocycles, 9, 153 (1978).

    Article  CAS  Google Scholar 

  18. T. Sano, J. Synth. Org. Chem., 42, 340 (1984).

    Article  CAS  Google Scholar 

  19. K. Nakanishi, Infrared Spectra and Structure of Organic Compounds [Russian translation], Mir, Moscow (1965), p. 45.

    Google Scholar 

  20. N. N. Polygalova, A. G. Mikhailovskii, and M. I. Vakhrin in: V. G. Kartsev (editor), The Chemistry and Biological Activity of Synthetic and Natural Compounds. Nitrogen Containing Heterocycles, Vol. 1, ICSPF Press, Moscow (2006), p. 402.

Download references

Author information

Authors and Affiliations

  1. Perm’ State Pharmaceutical Academy, 2 Polevaya St., Perm, 614990, Russia

    A. G. Mikhailovskii, O. V. Surikova, P. A. Chugainov & M. I. Vakhrin

Authors
  1. A. G. Mikhailovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. V. Surikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. P. A. Chugainov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. I. Vakhrin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. G. Mikhailovskii.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1046-1051, July, 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mikhailovskii, A.G., Surikova, O.V., Chugainov, P.A. et al. Acylation reaction of the 3,3-dimethylisoquinoline series enaminonitrile and properties of 5,5-dimethyl- 2,3-dioxo-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline- 1-carbonitrile. Chem Heterocycl Comp 49, 974–979 (2013). https://doi.org/10.1007/s10593-013-1334-x

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-013-1334-x

Keywords

Search

Navigation