Skip to main content
SpringerLink
Log in

Synthesis and study of the reactions of 2,5- and 1,2,5-substituted 6-aminoindoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

It has been shown that nitration with a KNO3 + H2SO4 mixture of 2,5-dimethyl- and 5-methyl-2-phenylindoles proceeds strictly selectively with the formation of 6-nitro derivatives, by reduction of which the corresponding aminoindoles were synthesized. It was established that the condensation of the aminoindoles obtained with β-diketones leads initially to enamino ketones, which in the presence of various acidic reagents are not subject to cyclization, i.e. may not be used for the synthesis of the corresponding pyrroloquinolines.

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. S. A. Yamashkin and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., 1587 (2001). [Chem. Heterocycl. Comp., 37, 1439 (2001)].

    Google Scholar 

  2. V. G. Kaitscv (editor), Selected Methods of Synthesis and Modyication of Heteroeycles. Vol. 3, Chemistry of Synthetic Indole Systems [in Russian], IBS PRESS, Moscow (2004), 594 pp.

    Google Scholar 

  3. V. A. Budylin, L. G. Yudin, and A. N. Kost, Khim. Geterotsikl. Soedin., 1181 (1980). [Chem. Heterocycl. Comp., 16, 887 (1980)].

  4. P. B. Terentiev, Mass Spectrometry in Organic Chemistry [in Russian], Vyssh. Shko1., Moscow (1979), 223 pp.

    Google Scholar 

  5. S. A. Yamashkin and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., 1336 (1999). [Chem. Heterocycl. Comp., 35, 1156 (1999)].

  6. S. A. Yamashkin and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., 1630 (1999). [Chem. Heterocycl. Comp., 35, 1426 (1999)].

  7. S. A. Yamashkin, E. A. Oreshkina, and N. V. Zhukova, Khim. Geterotstkl. Soedin., 1234 (2007). [Chem. Heteroeyel. Comp., 43, 1044 (2007)].

Download references

Author information

Authors and Affiliations

  1. M. E. Evsevʼev Mordovian State Pedagogical Institute, Saransk, 430007, Russia

    S. A. Yamashkin, N. N. Artaeva & E. A. Alyamkina

Authors
  1. S. A. Yamashkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. N. Artaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. A. Alyamkina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. A. Yamashkin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 529-537, April, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yamashkin, S.A., Artaeva, N.N. & Alyamkina, E.A. Synthesis and study of the reactions of 2,5- and 1,2,5-substituted 6-aminoindoles. Chem Heterocycl Comp 46, 419–425 (2010). https://doi.org/10.1007/s10593-010-0526-x

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-010-0526-x

Keywords

Search

Navigation