Synthesis of Pyrazolylquinoxalines and Pyrazolylpyrrolo[1,2-a]-quinoxalines

Pyrazolylquinoxaline류 및 Pyrazolylpyrrolo[1,2-a]-quinoxaline류의 합성

  • Kim, Ho Sik (Department of Chemistry, Catholic University of Taegu) ;
  • Lee, Seong Uk (Department of Chemistry, Catholic University of Taegu) ;
  • Jeong, Won Young (Department of Chemistry, Catholic University of Taegu) ;
  • Han, Sung Wook (Department of Environmental Engineering, Kyungwoon University) ;
  • Kim, Dong Il (Department of Environmental Engineering, Kyungwoon University) ;
  • Yoshihisa Kurasawa (School of Pharmaceutical Sciences, Kitasato University)
  • 김호식 (대구가톨릭대학교 자연과학대학 화학과) ;
  • 이성욱 (대구가톨릭대학교 자연과학대학 화학과) ;
  • 정원영 (대구가톨릭대학교 자연과학대학 화학과) ;
  • 한성욱 (경운대학교 환경공학과) ;
  • 김동일 (경운대학교 환경공학과) ;
  • Published : 20010800

Abstract

The reaction of 6-chloro-2-hydrazinoquinoxaline(4) or 6-chloro-2-hydrazinoquinoxaline 4-oxide(7) with alkyl (ethoxymethylene)cyanoacetates gave pyrazolylquinoxalines(5, 8). The reaction of compounds 8 with dimethyl acetylenedicarboxylate resulted in the 1,3-dipolar cycloaddition reaction and then ring transformation to afford pyrazolylpyrrolo[1,2-a]quinoxalines(9).

6-Chloro-2-hydrazinoquinoxaline(4) 또는 6-chloro-hydrazinoquinoxaline 4-oxide(7)를 alkyl(ethoxymethylene)cyanoacetate류와 반응시켜 prazolylquinoxaline류(5,8)를 합성하였다. 그리고 화합물 8을 dimethyl acethylenedicarboxylate와 반응시켜 1,3-쌍극성 고 리와 첨가반응과 고리변환에 의하여 pyrazolylpyrrolo[1,2-a]quinoxaline류(9)를 합성하였다.

Keywords

References

  1. J. Comprehensive Heterocyclic Chemistry II v.3 (a) Elguero, J. Comprehensive Heterocyclic Chemistry (A. R., Rees, C. W., Scriven, E. F., Eds.)
  2. The Chemistry of Heterocyclic Compounds, Condensed Pyrazines Cheeseman, C. W. H.; Cookson, R. F.(Weissberger, A., Taylor, E. C., Eds.)
  3. J. Heterocyclic Chem. v.37 Kim, H. S.; Kwag, S. T.; Choi, K. O.; Okamoto, Y.; Kajiwara, S.; Fujiwara, N.; Kurasawa, Y.
  4. J. Heterocyclic Chem. v.26 Kim, H. S.; Kurasawa, Y.; Takada, A.
  5. J. Heterocyclic Chem. v.27 Kim, H. S.; Kurasawa, Y.; Yoshii, C.; Masuyama, M.; Takada, A.; Okamoto, Y.
  6. J. Heterocyclic Chem. v.27 Kim, H. S.; Kurasawa, Y.; Yoshii, C.; Masuyama, M.; Takada, A.; Okamoto, Y.
  7. J. Org. Chem. v.11 Fuson, R. C.; Parham, W. E.; Reed, L. J.
  8. J. Am. Chem. Soc. v.73 Jones, R. G.
  9. J. Am. Chem. Soc. v.74 Jones, R. G.
  10. Organic Syntheses v.3 Horning, E. C.(W. E., Reed, L. J., Eds.)
  11. J. Heterocyclic Chem. v.27 Kim, H. S.; Kurasawa, Y.; Yoshii, C.; Masuyama, M.; Takada, A.; Okamoto, Y.