Skip to main content
SpringerLink
Log in

Annelation of lactam rings to 2,3,4,4a-tetrahydro-1H-carbazole derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

In the reaction of 4a-methyl-2,3,4,4a-tetrahydro-1H-carbazole and its 6-methyl- and 6-bromosubstituted derivatives with 2-chloroacetamide respectively by 9-carbamoylmethyl-4a-methyl-2,3,4,4a-tetrahydro-1H-carbazolium chlorides are formed, which can be cyclized into 5,6,7,7a-tetrahydro-1H, 4H-imidazo[2,1-k]-carbazol-2(3H)-one derivatives. Reaction of 4a-methyl-2,3,4,4a-tetrahydro-1H-carbazole hydrochloride with acrylamide gives 8a-methyl-1,2,6,7,8,8a-hexahydro-5H-pyrimido[2,1-k]carbazol-3(4H)-one. 7a, 12-Dimethyl-3,4,4a,5,6,7,7a,12-octahydropyrido[3,2-j]carbazol-2(1H)-one was synthesized by the reaction of 4a,9-dimethyl-2,3,4,4a-tetrahydro-9H-carbazole with acrylamide.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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. A. Degutis, A. A. Shachkus, and A. G. Urbonavichyus,Khim. Geterotsikl. Soedin., No. 7, 933 (1985).

    Google Scholar 

  2. A. A. Shachkus and Yu. A. Degutis,Khim. Geterotsikl. Soedin., No. 11, 1485 (1986).

    Google Scholar 

  3. A. A. Shachkus and R. Yu. Degute,Khim. Geterotsikl. Soedin., No. 8, 1056 (1986).

    Google Scholar 

  4. A. A. Shachkus and Yu. A. Degutite,Khim. Geterotsikl. Soedin., No. 5, 625 (1990).

    Google Scholar 

  5. A. A. Shachkus and Yu. A. Degutis,Khim. Geterotsikl. Soedin., No. 7, 902 (1988).

    Google Scholar 

  6. C. McCarty and K. Jones,J. Chem. Soc. Chem. Commun. 1717 (1989).

  7. T. Oishi, M. Nagai, and Y. Ban,Tetrahedron Lett., No. 4, 491 (1968).

    Google Scholar 

  8. A. Azzouzi, B. Perrin, M.-E. Sinibaldi, D. Gardette, C. Lavaud, D. Vallee-Goyet, J.-C. Gramain, and A. Kerbal,Bull. Soc. chim. Fr.,132, 681 (1995).

    CAS  Google Scholar 

  9. J.-G. Rodriguez and A. San Andres,J. Heterocycl. Chem.,28, 1293 (1991.)

    CAS  Google Scholar 

Download references

Authors
  1. A. Šačkus
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Krikštolaityte
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. Martynaitis
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Department of Organic Chemistry, Kaunas University of Technology, Kaunas LT-3028, Lithuania; Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 645–648, May 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Šačkus, A., Krikštolaityte, S. & Martynaitis, V. Annelation of lactam rings to 2,3,4,4a-tetrahydro-1H-carbazole derivatives. Chem Heterocycl Compd 35, 575–579 (1999). https://doi.org/10.1007/BF02324641

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02324641

Keywords

Search

Navigation