Skip to main content
SpringerLink
Log in

Reactivity of 4-bromomethylquinoline derivatives towards glycine and thioglycolic acid. A new ring system

Die Reaktivität von 4-Brommethylchinolin-Derivaten gegenüber Glycin und Thioglycolsäure. Ein neues Ringsystem

  • Organische Chemie und Biochemie
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Condensation of 4-bromomethylquinoline derivatives1 a-1 c with glycine and thioglycolic acid gave the corresponding quinolylmethylglycine and quinolylmethylthioacetic acid derivatives2 a-2 c and2 d-2 f, respectively. Cyclization of2 a-2 f was affected either by polyphosphoric acid or concentrated sulphuric acid to give3 a-3 f. Chlorination of2 a-2 f and3 a-3 f were also accomplished.

Zusammenfassung

Die Reaktion von 4-Brommethylchinolin-Derivaten1 a-c mit Glycin und Thioglycolsäure gab die entsprechenden Kondensationsprodukte2 a-c und2d-f.2 a-f konnten mit Polyphosphorsäure bzw. mit konzentrierter Schwefelsäure zu Benzo[c]-2,6-naphthyridinen3 a-f zyklisiert werden.2 a-f und3 a-f waren einer Chlorierung (POCl3) zugängig.

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. J. H. Burckhalter, R. Leib, andY. S. Chough, J. Med. Chem.6, 89 (1963).

    Article  CAS  Google Scholar 

  2. A. R. Katritzky andA. J. Boulton, Advances in Heterocyclic Chemistry, Vol. 11, p. 154. New York: Academic Press. 1970.

    Google Scholar 

  3. W. Ried andF. Kohlhass, Ann. Chem.707, 242 (1967).

    Article  CAS  Google Scholar 

  4. R. B. Woodward, N. C. Yang, andT. J. Katz, Proc. Chem. Soc.1960, 76.

  5. G. Giacomello, F. Gualtieri, F. M. Riccieri, andM. L. Stein, Tetrahedron Lett.1965, 1117.

  6. R. Tan andA. Taurins, Tetrahedron Lett.1965, 2737.

  7. R. J. Chudgar andK. N. Trivedi, J. Ind. Chem. Soc.46, 537 (1969).

    CAS  Google Scholar 

  8. G. C. Wright, E. J. Watson, F. F. Ebetino, G. Lougheed, B. F. Stevenson, A. Winterstein, R. K. Bickerton, R. P. Halliday, andD. T. Pals, J. Med. Chem.14, 1060 (1971).

    Article  CAS  Google Scholar 

  9. S. Archer andA. Murabayashi, Tetrahedron Lett.1969, 2449.

Download references

Author information

Authors and Affiliations

  1. National Research Centre, Dokki, Cairo, Egypt

    M. Nasr, A. Zayed & M. T. El-Wassimi

  2. Faculty of Science, Mansoura University, Mansoura, Egypt

    H. H. Zoorob

Authors
  1. M. Nasr
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. H. H. Zoorob
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Zayed
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. T. El-Wassimi
    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

Nasr, M., Zoorob, H.H., Zayed, A. et al. Reactivity of 4-bromomethylquinoline derivatives towards glycine and thioglycolic acid. A new ring system. Monatshefte für Chemie 110, 913–918 (1979). https://doi.org/10.1007/BF00906688

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00906688

Keywords

Search

Navigation