Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis of Tetrazolo[1,5-a]quinoxalines with Antimicrobial Activity

항균성을 가진 Tetrazolo[1,5-a]quinoxaline류의 합성

  • Kim, Ho Sik (Department of Chemistry, Catholic University of Taegu) ;
  • Kim, Dong Eun (Department of Chemistry, Catholic University of Taegu) ;
  • Yoshihisa Kurasawa (School of Pharmaceutical Sciences, Kitasato University)
  • 김호식 (대구가톨릭대학교 자연과학대학 화학과) ;
  • 김동은 (대구가톨릭대학교 자연과학대학 화학과) ;
  • Published : 20010800
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Abstract

The 4-substituted tetrazolo[1,5-a]quinoxalines were synthesized from 4-chlorotetrazolo-[1,5-a]quinoxaline(8) or 4-hydrazinotetrazolo[1,5-a]quinoxaline(9). Refluxing of the tetrazolo[1,5-a]quinoxaline(12) in N,N-dimethylformamide gave the 1,2,4-triazolo[3,4-c]tetrazolo[1,5-a]quinoxaline(13), which was also obtained by the reaction of compound 9 with ethyl chloroformate in N,N-dimethylformamide. The reaction of compound 9 with isothiocyanates in ethanol provided the tetrazolo[1,5-a]quinoxalines(14), whose reaction with dimethyl acetylenedicarboxylate afforded the tetrazolo[1,5-a]quinoxalines(15). The tetrazolo [1,5-a]quinoxalines(18) were obtained by the reaction of compound 9 with alkyl (ethoxymethylene)cyanoacetates. Some of the compounds showed antibacterial, antifungal or algicidal activities against some strains.

4-치환 tetrazolo[1,5-a]quinoxaline류는 4-chlorotetrazolo[1,5-a]quinoxaline(8) 또는 4hydra-zino-[1,5-a]quinoxaline(9)으로부터 합성하였다. N,N-디메틸포름아미드 용매에서 tetrazololo[1,5-a]quinoxaline(12)를 환류시켜 1,2,4-triazolo[3,4-c]tetrazolo[1,5-a]quinoxaline (13)을 합성하였으며, 이것은 N,N-디메틸포름아미드 용매에서 화합물 9와 ethyl chloroformate를 반응시켜도 합성할 수 있었다. 화합물 9를 isothiocyanate류와 반응시켜 tetrazololo[1,5-a]quinoxaline류(14)를 합성하였으며, 이것을 dimethyl acethylenedicarboxyla-te와 반응시켜 tetrazololo[1,5-a]quinoxaline류(15)를 합성하였다. 그리고 화합물 9를 alkyl (ethoxymethylene)-cyanoacetate류와 반응시켜 tetrazololo[1,5-a]quinoxaline류(18)를 합성하였다. 합성한 화합물 중에서 몇 가지는 몇 가지 균주에 대하여 항균성, 항진균성 도는 항조류성을 나타내었다.

Keywords

References

  1. Comprehensive Heterocyclic Chemistry II v.4 (a) Garratt, P. J. (Katritzky, A. R., Rees, C. W., Scriven, E. F. V.,Eds.)
  2. The Chemistry of Heterocyclic Compounds. Condensed Pyrazines Cheesman, C. W. H.; Cookson, R. F. (Weissberger, A., Taylor, E. C., Eds.)
  3. J. Heterocyclic Chem. v.26 Kim, H. S.; Kurasawa, Y.; Takada, A.
  4. J. Heterocyclic Chem. v.30 Kurasawa, Y.; Kureyama, T.; Yoshishiba, N.; Okano, T.; Takada, A.; Kim, H. S.; Okamoto, Y.
  5. J. Heterocyclic Chem. v.30 Kurasawa, Y.; Yoshishiba, N.; Kureyama, T.; Takada, A.; Kim, H. S.; Okamoto, Y.
  6. J. Heterocyclic Chem. v.30 Kurasawa, Y.; Matsumoto, Y.; Ishikura, A.; Ikeda, K.; Hosaka, T.; Takada, A.; Kim, H. S.; Okamoto, Y.
  7. J. Heterocyclic Chem. v.26 Kim, H. S.; Kurasawa, Y.; Takada, A.
  8. J. Heterocyclic Chem. v.27 Kim, H. S.; Kurasawa, Y.; Yoshii, C.; Masuyama, M.; Takada, A.; Okamoto
  9. J. Heterocyclic Chem. v.33 Kim, H. S.; Chung, J. Y.; Kim, E. K.; Park, Y. T.; Hong, Y. S.; Lee, M. K.; Kurasawa, Y.; Takada, A.
  10. J. Heterocyclic Chem. v.37 Kim, H. S.; Kwag, S. T.; Choi, K. O.; Okamoto, Y.; Kajiwara, S.; Fujiwara, N.; Kurasawa, Y.
  11. J. Chem. Soc. Phillips, M. A.
  12. Recl. Trav. Chim. Pays-Bas. v.77 Mager, H. I. X.; Berends, W.
  13. J. Chem. Soc. Cheeseman, G. W. H.
  14. Nippon Kagaku Kaishi Tomoda, H.; Saito, S.; Ohishi, M.; Shiraishi, S.
  15. Yakugaku Zasshi v.78 Asano, K.
  16. Ind. J. Chem. v.30B Reddy Sastry, C. V.; Krishnan, V. S. H.; Narayan, G. K. A. S. S.; Vemana, K.
  17. E. Z. Chem. v.18 Konnecke, A.; Lippmann
  18. Heterocycles v.41 Kurasawa, Y.; Takada, A.; Kim, H. S.
  19. J. Org. Chem. v.11 Fuson, R. C.; Parham, W. E.; Reed, L. J.
  20. J. Am. Chem. Soc. v.73 Jones, R. G.
  21. J. Am. Chem. Soc. v.74 Jones, R. G.
  22. Organic Syntheses v.3 Horning, E. C.(Parham, W. E., Reed, L. J., Eds.)