Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis and Tautomerism of Pyrazoles and N-Phenylethanamides with Quinoxaline Ring

Quinoxaline 고리를 가진 Pyrazole류 및 N-Phenylethanamide류의 합성과 토토머화 현상

  • Kim, Ho Sik (Department of Chemistry, Catholic University of Taegu) ;
  • Choi, Kyung Ok (Department of Chemistry, Catholic University of Taegu) ;
  • Lee, Hyong Choul (Department of Chemistry, Catholic University of Taegu) ;
  • Kwag, Sam Tag (Division of Chemical Engineering, Pukyong National University) ;
  • Yoshihisa Kurasawa (School of Pharmaceutical Sciences, Kitasato University)
  • 김호식 (대구가톨릭대학교 자연대 화학과) ;
  • 최경옥 (대구가톨릭대학교 자연대 화학과) ;
  • 이형철 (대구가톨릭대학교 자연대 화학과) ;
  • 곽삼탁 (부경대학교 화학공학부) ;
  • Published : 20011000
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Abstract

The reaction of 3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(7) with hydrazine hydrate gave 3-hydrazinocarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(8). The reaction of compound 8 with alkyl (ethoxymethylene)cyanoacetates gave the [(quinoxalin-2-ylidene)ethanoyl]-1H-pyra-zoles(9). The reaction of compound 9b with N-alkylanilines provided the N-alkyl-(quinoxalin-2-ylidene)-N-phenylethanamides(10). Compounds 9 and 10 showed the tautomerism between the enamine and methylene imine forms in solution. The tautomer ratios were determined by the $^1H$ NMR.

3-Methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(7)을 hydrazine hydrate와 반응시켜 3-hydrazinocarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline(8)을 합성하였다. 화합물 8을 alkyl (ethoxymethylene)cyanoacetate류와 반응시켜 [(quinoxalin-2-ylidene)ethanoyl]-1H-pyrazole류(9)를 합성하였고, 화합물 9b를 N-alkylaniline류와 반응시켜 N-alkyl-(quinoxalin-2-ylidene)-N-phenylethanamide류(10)를 합성하였다. 얻어진 화합물 9, 10은 용액에서 enamine 형과 methylene imine 형 사이에 토토머화 현상을 나타내었는데, 이들의 토토머비를 $^1H$ NMR 로서 측정하였다.

Keywords

References

  1. Comprehensive Heterocyclic Chemistry Ⅱ v.3 Elguero, J.;Katrizky, A. R.(ed.);Rees, C. W.(ed.);Scriven, E. F. V.(ed.)
  2. Comprehensive Heterocyclic Chemistry Ⅱ v.6 Sato, N.;Katrizky, A. R.(ed.);Rees, C. W.(ed.);Scriven, E. F. V.(ed.)
  3. The Chemistry of Heterocyclic Compounds. Condensed Pyrazines Cheeseman, G. W. H.;Cookson, R. F.;Weissberger, A.(ed.);Taylor, E. C.(ed.)
  4. Ind. J. Heterocyclic Chem. v.5 Ankhiwala, M. D.;Hathi, M. V.
  5. Ind. J. Chem. v.30B Awad, I. M. A.
  6. Chem. Pharm. Bull. v.47 Kudo, N.;Furuta, S.;Taniguchi, M.;Endo, T.;Sato, K.
  7. Heterocycles v.26 Makino, K.;Yoshioka, H.
  8. Chem. Pharm. Bull. v.45 Tsuji, K.;Nakamura, K.;Konishi, N.;Tojo, T.;Ochi, T.;Senoh, H.;Matsuo, M.
  9. J. Heterocyclic Chem. v.26 Monge, A.;Palop, J. A.;Urbasos, I.;Fern ndez-Alvarez, E.
  10. J. Heterocyclic Chem. v.26 Kurasawa, Y.;Kim, H. S.;Yonekura, K.;Takada, A.;Okamoto, Y.
  11. J. Heterocyclic Chem. v.26 Kim, H. S.;Kurasawa, Y.;Takada, A.
  12. J. Heterocyclic Chem. v.27 Kim, H. S.;Kurasawa, Y.;Yoshii, C.;Masuyama, M.;Takada, A.;Okamoto, Y.
  13. J. Heterocyclic Chem. v.29 Kurasawa, Y.;Katoh, R.;Mori, F.;Fukuchi, M.;Okamoto, M.;Takada, A.;Kim, H. S.;Okamoto, Y.
  14. J. Heterocyclic Chem. v.33 Kurasawa, Y.;Takano, A.;Kato, K.;Takada, A.;Kim, H. S.;Okamoto, Y.
  15. 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.
  16. J. Heterocyclic Chem. v.37 Kim, H. S.;Kwag, S. T.;Choi, K. O.;Okamoto, Y.;Kajiwara, S.;Fujiwara, N.;Kurasawa, Y.
  17. J. Korean Chem. Soc. v.44 Kim, H. S.;Kwag, S. T.
  18. J. Org. Chem. v.11 Fuson, R. C.;Parham, W. E.;Reed, L. J.
  19. J. Am. Chem. Soc. v.73 Jones, R. G.
  20. J. Am. Chem. Soc. v.74 Jones, R. G.
  21. Organic Syntheses v.Collective 3 Horning, E. C.;Parham, W. E.(ed.);Reed, L. J.(ed.)
  22. Nippon Kagaku Zasshi v.82 Iwanami, Y.
  23. Ann. Chem. v.658 Weygard, F.;Steglich, W.;Tanner, H.
  24. J. Chem. Soc. Perkin Trans. v.1 Suschitzky, H.;Wakefeld, B. J.;Whittker, R. A.
  25. Synthesis Kurasawa, Y.;Moritaki, Y.;Takada, A.
  26. Chem. Pharm. Bull. v.31 Kurasawa, Y.;Moritaki, Y.;Ebukuro, T.;Takada, A.
  27. J. Heterocyclic Chem. v.34 Kim, H. S.;Kim, E. K.;Kim, S. S.;Park, Y. T.;Hong, Y. S.;Kurasawa, Y.
  28. Heterocycles v.41 Kurasawa, Y.;Takada, A.;Kim, H. S.
  29. J. Korean Chem. Soc. v.44 Kim, H. S.;Choi, K. O.;Kurasawa, Y.