Skip to main content
Log in

Oxadiazole condensed ring systems, I: Synthesis of 1,3,4-oxadiazolo[3,2-a]pyrimidin-5-ones as possible antimicrobial agents

Kondensierte Ringsysteme des Oxadiazols, 1. Mitt.: Synthese von 1,3,4-Oxadiazolo[3,2-a]pyrimidin-5-onen als potentiell antimikrobielle Substanzen

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

Syntheses of some substituted 7-hydroxy-5H-1,3,4-oxadiazolo[3,2-a]pyrimidin-5-ones (3) and their 7-methoxy (4), 7-chloro (5) and 7-azido (6) derivatives are described. 2-Phenyl-N,N′-bis(3-tolyl)propanediamide (8) was obtained, instead of the expected triazolopyrimidinone7 upon reacting3b withm-toluidine. Three compounds were screened forin vitro antibacterial and antifungal activities.

Zusammenfassung

Die Synthese einiger substituierter 7-Hydroxy-5H-1,3,4-oxadiazolo[3,2-a]-pyrimidin-5-one (3) und ihrer 7-methoxy (4), 7-chloro (5) und 7-azido (6) Derivate wird beschrieben. Anstelle des erwarteten Triazolo-pyrimidinons7 entsteht bei der Reaktion von3b mitm-Toluidin 2-Phenyl-N,N′-bis(3-tolyl)-propandiamid (8). Drei Verbindungen wurden auf antimikrobakterielle und fungizide Wirkung geprüft.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Ziegler E., Wolf R. (1962) Monatsh. Chem.93: 1441

    Google Scholar 

  2. Gehlen H., Simon B. (1970) Arch. Pharm.303: 501

    Google Scholar 

  3. Henklein P., Westphal G., Kraft R. (1973) Tetrahedron29: 2937

    Google Scholar 

  4. Sakamoto M., Miyazawa K., Tomimatsu Y. (1977) Chem. Pharm. Bull.25: 3360

    Google Scholar 

  5. Bhattacharya B. K., Hoornaert G. (1984) Chem. Scr.23: 90; (1984) C. A.101: 55031v

    Google Scholar 

  6. Valsula T. R., Srimivasen V. R. (1971) Indian J. Chem.9: 901

    Google Scholar 

  7. Sakamoto M., Miyazawa K., Tomimatsu Y., (1976) Chem. Pharm. Bull.24: 2532

    Google Scholar 

  8. Mir I., Siddiqui M. T., Comrie A. M. (1971) J. Chem. Soc. (c): 2798

  9. Sen Gupta A. K., Bajaj O. P., Chandra U. (1978) J. Indian Chem. Soc.55: 962

    Google Scholar 

  10. Daluge S. M., Skonezny P. M., Roth B., Rauchmann B. S. (1984) Eur. Pat. (Cl. A61 K31/505); (1984) C. A.100: 139135z

  11. Kawaskima M. (1959) Chem. Pharm. Bull.7: 13

    Google Scholar 

  12. Nishimura T., Fujita S., Tanak A., Matsumoto K., Kawukami M., Fukuyasu H., Fukuyasu T., Kazuno Y., Watnabe T. (1979) Bokin Bobai7: T 159; (1979) C. A.91: 211359r

  13. Gehlen H., Simon B. (1970) Arch. Pharm.303: 511

    Google Scholar 

  14. Conducted in the Department of Microbiology, Medical Research Institute, University of Alexandria, Egypt

  15. Kappe T. (1967) Monatsh. Chem.98: 874

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Badawey, ES.A.M., Hassan, A.M.M. & Soliman, F.S.G. Oxadiazole condensed ring systems, I: Synthesis of 1,3,4-oxadiazolo[3,2-a]pyrimidin-5-ones as possible antimicrobial agents. Monatsh Chem 121, 665–669 (1990). https://doi.org/10.1007/BF00809770

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00809770

Keywords

Navigation