Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis of 2-(Pyrazol-1-yl)quinoxalines and 2,3-Di(pyrazol-1-yl)quinoxalines

2-(Pyrazol-1-yl)quinoxaline류 및 2,3-Di(pyrazol-1-yl)quinoxaline류의 합성

  • 김호식 (대구가톨릭대학교 자연대학 화학과) ;
  • 정원영 (대구가톨릭대학교 자연대학 화학과) ;
  • 최경옥 (대구가톨릭대학교 자연대학 화학과) ;
  • 이성욱 ;
  • 곽삼탁 (부경대학교 화학공학부) ;
  • 이만길 (고신대학교 화학과)
  • Published : 2002.02.20
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Abstract

The reaction of 3,6-dichloro-2-(3,5-dimethylpyrazol-1-yl)quinoxaline(8) or 6-chloro-3-hydrazino-2-(3,5-dimethylpyrazol-1-yl)quinoxaline(9) with substituted anilines, sulfa drugs and heteroacyl chlorides gave 2-(pyrazol-1-yl)quinoxalines(10-12). The reaction of compound 9 with alkyl (ethoxymeth-ylene) cyanoacetates resulted in the intramolecular cyclization to give 2,3-di(pyrazol-1-yl)quinoxalines(13).

3,6-Dichloro-2-(3,5-dimethylpyrazol-1-yl)quinoxaline(8)또는 6-chloro-3-hydrazino-2-(3,5-dimethylpyrazol-1-yl)quinoxaline(9)을 치환 아닐린류, 슬파제 및 heteroacyl chloride류와 반응시켜 2-(pyrazol-1-yl)quinoxaline류(10-12)를 합성하였다. 그리고 화합물 9를 alkyl (ethoxymethylene)cyanoacetate류와 반응시켜 분자내 고리화반응에 의하여 2,3-di(pyrazol-1-yl)quinoxaline류(13)를 합성하였다.

Keywords

References

  1. Elguero, J. Comprehensive Heterocyclic Chemistry II; Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, U. K., 1996, Vol. 3, pp. 1-75.
  2. Sato, N. Comprehensive Heterocyclic Chemistry II;Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.;Pergamon Press: Oxford, U. K., 1996, Vol. 6, pp. 234-278.
  3. Cheeseman, G. W. H.; Cookson, R. F. The Chemistry of Heterocyclic Compounds, Condensed Pyrazines; Weissberger, A., Taylor, E. C., Eds.; John Wiley & Sons: New York, U. S. A., 1979; pp 1-290.
  4. Tsuji, K.; Nakamura, K.; Konishi, N.; Tojo, T.; Ochi, T.; Senoh, H.; Matsuo, M. Chem. Pharm. Bull. 1997, 45, 987. https://doi.org/10.1248/cpb.45.987
  5. Kudo, N.; Furuta, S.; Taniguchi, M.; Endo, T.; Sato, K.Chem. Pharm. Bull. 1999, 47, 857. https://doi.org/10.1248/cpb.47.857
  6. Kim, H. S.; Kurasawa, Y.; Takada, A. J. Heterocyclic Chem. 1989, 26, 1511. https://doi.org/10.1002/jhet.5570260550
  7. Kim, H. S.; Kurasawa, Y.; Yoshii, C.; Masuyama, M.; Takada, A.; Okamoto, Y. J. Heterocyclic Chem. 1990, 27, 1111. https://doi.org/10.1002/jhet.5570270456
  8. Kim, H. S.; Chung, J. Y.; Kim, E. K.; Park, Y. T.; Hong,Y. S.; Lee, M. K.; Kurasawa, Y.; Takada, A. J. Heterocyclic Chem. 1996, 33, 1855. https://doi.org/10.1002/jhet.5570330649
  9. Kim, H. S.; Kwag, S. T.; Choi, K. O.; Okamoto, Y.;Kajiwara, S.; Fujiwara, N.; Kurasawa, Y. J. Heterocyclic Chem. 2000, 37, 103. https://doi.org/10.1002/jhet.5570370116
  10. Kim, H. S.; Kwag, S. T. J. Korean Chem. Soc. 2000,44, 229.
  11. Kim, H. S.; Lee, S. U.; Jeong, W. Y.; Han, S. W.; Kim,D. I.; Kurasawa, Y. J. Korean Chem. Soc. 2001, 45,318.
  12. Kim, H. S.; Choi, K. O.; Lee, H. C.; Kwag, S. T.; Kurasawa, Y. J. Korean Chem. Soc. 2001, 45, 454.
  13. Fuson, R. C.; Parham, W. E.; Reed, L. J. J. Org. Chem.1946, 11, 194. https://doi.org/10.1021/jo01172a014
  14. Jones, R. G. J. Am. Chem. Soc. 1951, 73, 3684. https://doi.org/10.1021/ja01152a034
  15. Jones, R. G. J. Am. Chem. Soc. 1952, 74, 4889. https://doi.org/10.1021/ja01139a046
  16. Horning, E. C. Organic Syntheses; Parham, W. E., Reed,L. J., Eds.; John Wiley & Sons: New York, U. S. A.,1995; Collective Vol. 3, pp 395-397.
  17. Delgado, J. N.; Remers, W. A. Textbook of Organic Medicinal and Pharmaceutical Chemistry, 9th Ed.; J. B. Lippincott Co.: Philadelphia, U. S. A., 1991; pp 197-201.

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