Skip to main content
SpringerLink
Log in

New functionalization opportunities for peri-hydroxynaphthoyl and peri-fused heterocyclic compounds

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

A capability was studied of hydrogenated α-pyrone heterocycle in 7-methoxy-4-(4-methoxy-phenyl)-3,4-dihydro-2H-benzo[h]chromen-2-one to undergo aminolysis under the treatment with hydrazine hydrate, primary and secondary aliphatic and aromatic amines. A new approach was developed to the preparation of perihydroxyketone of naphthalene series containing a specific functional substituent in the ortho-position with respect to hydroxy group. The effect was revealed of an acetyl group in the position 9 of 7-methoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-benzo[h]chromen-2-one on the reaction of this compound with aliphatic amines and hydrazine hydrate. 9-Methoxy-1-(4-methoxyphenyl)-6-methyl-3H-benzo[de]pyrido[3,2,1-if]cinnolin-3-one [9-methyl-6-methoxy-3-(4-methoxyphenyl)-10,10a-diazapyren-1-one] was obtained, a new bis-peri-fused heteroaromatic system.

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. Tkachenko, V.V., Zhukovskaya, O.N., Mezheritskii, V.V., and Dorofeenko, G.N., Zh. Org. Khim., 1977, vol. 13, p. 2009.

    CAS  Google Scholar 

  2. Mezheritskii, V.V. and Tkachenko, V.V., Synthesis of periannelated Heterocyclic Systems. Advances in Heterocyclic Chemistry, New York: Academic Press, 1990, 51, p. 1.

    Google Scholar 

  3. Mezheritskii, V.V., Tyurin, R.V., Minyaeva, L.G., Antonov, A.N., Zadorozhnaya, A.P., Zh. Org. Khim., 2006, vol. 42, p. 1473.

    Google Scholar 

  4. Bellamy, L.J., The Infra Red Spectra of Complex Molecules, London: Methuen, 1958.

    Google Scholar 

  5. Mezheritskii, V.V., Khimiya 1N-1,2-diazofenalena (Chemistry of 1N-1,2-diazophenalene), Kartseva, V.G., Ed., Moscow: Iridium-Press, 2001, p. 112.

    Google Scholar 

  6. Borovlev, I.V. and Demidov, O.P., Khim. Geterotsikl. Soedin., 2003, p. 1612.

  7. Mezheritskii, V.V., Tkachenko, V.V., Zhukovskaya, O.N., Eliseevich, D.M., and Dorofeenko, G.N., Zh. Org. Khim., 1981, vol. 17, p. 627.

    CAS  Google Scholar 

  8. Mezheritskii, V.V., Minyaeva, L.G., and Tyurin, R.V., Izv. Akad. Nauk, Ser. Khim., 2005, p. 777.

Download references

Author information

Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry at Southern Federal University, Rostov-on-Don, 344090, Russia

    R. V. Tyurin, A. P. Zadorozhnaya, A. N. Antonov & V. V. Mezheritskii

Authors
  1. R. V. Tyurin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. P. Zadorozhnaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. N. Antonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. V. Mezheritskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. V. Mezheritskii.

Additional information

Original Russian Text © R.V. Tyurin, A.P. Zadorozhnaya, A.N. Antonov, V.V. Mezheritskii, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 11, pp. 1680–1687.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tyurin, R.V., Zadorozhnaya, A.P., Antonov, A.N. et al. New functionalization opportunities for peri-hydroxynaphthoyl and peri-fused heterocyclic compounds. Russ J Org Chem 44, 1657–1664 (2008). https://doi.org/10.1134/S1070428008110171

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428008110171

Keywords

Search

Navigation