Skip to main content
SpringerLink
Log in

Synthesis of 2-(β-Hetarylaminoethyl)-3,5,6-trichloro-1,4-benzoquinones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

4,6,7-Trichloro-2-hetarylamino-5-hydroxy-2,3-dihydrobenzo[b]furans have been prepared from 4,6,7-trichloro-2,5-dihydroxy-2,3-dihydrobenzo[b]furan and hetarylamines. Reductive opening of the dihydrobenzofuran ring in these compounds gave 3,5,6-trichloro-2-(β-hetarylaminoethyl)hydroquinones. The latter could be oxidised to the target 3,5,6-trichloro-2-(β-hetarylaminoethyl)-1,4-benzoquinones which are novel 1,4-benzoquinone derivatives with intramolecular charge transfer.

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. G. A. Karlivan,R. E. Valter, and M. F. Utinan, Khim. Geterotsikl. Soedin., 849 (1985).

  2. R. E. Valter,G. A. Karlivan,M. F. Utinan, and Yu. V. Gulbis, Sib. Khim. Zh., No. 4, 39 (1992).

  3. R. Valters,G. Karlivans,J. Gulbis,M. Utinans, and A. Bace, Phosph., Sulfur and Silicon, 95 & 96, 457 (1994).

    Google Scholar 

  4. R. E. Valter,E. E. Liepin'sh,G. A. Karlivan,V. R. Zin'kovska, and M. F. Utinan, Zh. Org. Khim., 21, 436 (1985).

    Google Scholar 

  5. M. F. Utinan,R. E. Valter,G. A. Karlivan,E. E. Liepin'sh, and A. S. Edzhinya, Khim. Geterotsikl. Soedin., 692 (1988).

  6. M. F. Utinan,R. E. Valter, and G. A. Karlivan, Khim. Geterotsikl. Soedin., 1430 (1989).

  7. Yu. V. Gulbis,R. E. Valter,G. A. Karlivan, and M. F. Utinan, Khim. Geterotsikl. Soedin., 111 (1994).

  8. Yu. V. Gulbis and R. E. Valters, Khim. Geterotsikl. Soedin., 1556 (2001).

  9. G. Karlivans,J. Gulbis,R. Valters,A. Bace, and R. Kampare, Latv. J. Chem., 99 (1994).

  10. G. A. Karlivan,R. E. Valter, and Yu. V. Gulbis, Khim. Geterotsikl. Soedin., 1055 (1998).

  11. Ya. F. Freimanis, Organic Compounds with Intramolecular Charge Transfer [in Russian], Riga: Zinatne (1985).

    Google Scholar 

  12. M. R. Bryce, Adv. Mater., 11, 11 (1999).

    Google Scholar 

  13. E. Tsiperman,T. Regev,J. Y. Becker,J. Bernstein,A. Ellern,V. Khodorkovsky,A. Shames, and L. Shapiro, Chem. Commun., 1125 (1999).

  14. D. Buckley,H. B. Henbest, and P. Slade, J. Chem. Soc., 4891 (1957).

  15. D. Buckley,S. Dunstan, and H. B. Henbest, J. Chem. Soc., 4880 (1957).

  16. E. P. Fokin and E. P. Prudchenko, Zh. Org. Khim., 6, 1251 (1970).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Riga Technical University, Riga, LV-1048, Latvia

    G. Karlivans & R. Valters

Authors
  1. G. Karlivans
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. Valters
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Karlivans, G., Valters, R. Synthesis of 2-(β-Hetarylaminoethyl)-3,5,6-trichloro-1,4-benzoquinones. Chemistry of Heterocyclic Compounds 39, 1617–1622 (2003). https://doi.org/10.1023/B:COHC.0000018339.22815.13

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:COHC.0000018339.22815.13

Search

Navigation