Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis and Tautomerism of Pyrido[2,3-b]pyrazines

Pyriodo[2,3-b]pyrazine류의 합성과 토토머화 현상

  • Kim, Ho-Sik (Department of Chemistry Catholic University of Taegu-Hyosung) ;
  • Choi, Kyung-Ok (Department of Chemistry Catholic University of Taegu-Hyosung) ;
  • Kurasawa, Yoshihisa (School of Pharmaceutical Sciences, Kitasato University)
  • 김호식 (대구효성가톨릭대학교자연대 화학과) ;
  • 최경옥 (대구효성가톨릭대학교자연대 화학과) ;
  • Published : 20001000
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Abstract

The reaction of 2-methoxycarlmethylen-l,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(5) with hydrazine hydrate and ethylenediamine gave 2-hydrazinocarbonylmethylene-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(6) and 2-aminoethylcarbamethylene-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(7), res-pectively. The reaction of compound 6 or 7 with substituted benzaldehydes or heteroaryl aldehydes afforded pyrido[2,3-b]pyrazines(8-13). Some pyrin the enamine, methylene imine and enaminol forms in solution. The tau-tomer ratios were determined by the H NMR.

2-Methoxycarbonylmethylene-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(5)을 hydrazine hydrate와 ethylenediamine을 반응시켜 2-hydrazinocarbonylmethylene-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(6)과 2-aminoethylcarbamoylmethylene-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(7)을 각각 합성하였다. 화합물 6 또는 7을 치환 벤즈알데히드류 및 헤테로아릴 알데히드류와 반응시켜 pyrido[2,3-b]pyrazin류(8-13)를 각각 합성하였다. 몇가지 pyrido[2,3-b]pyrazin은 용액에서 enamine형,methylene imine형, methylene imine형,enaminol형 사이에 토토머화 현상을 나타내었는데, 이들의 토토머 비는 1H NMR로서 측정하였다.

Keywords

References

  1. 7he Chemistry of Hetenxyck Compounds. Condensed Pyrazines Cheeseman,G. W.H.; Cookson, R. F.;Weissberger, A.(Eds.);Taylor, E. C.(Eds.)
  2. Comprehensive Heterocyclic Chemistry v.3 Katritzky, A. R.; Rees, C. W.;Boulton, A. J.(Eds.); Mckillop, A.(Eds.)
  3. Chem, Pharm. Bull. v.22 Nakao, H.; Fukushinm M.; Yanagisawa,H.; Sugawara, S.
  4. Jpn. Kokai 1991, 03106880;Chem. Abstr. v.115 Masuda S.; Oohara, S.
  5. U. S. Patent 1979, 4138564;Chem. Abstr v.90 Freed, M.E.;Potoski, J. R.
  6. Eur. Patent1983, EP 90681; Chem. Abstr. v.100 Temple,C. G.; MontgorneIY, J. A.; E8iottjR D.; Wheeler,G. P.
  7. Heterocyclic Chem v.32 SeId, T.; Iwanami, Y. J.
  8. J. Heterocyclic Chem. v.30 kurasawa, Y.;Matsumoto, Y.;Ishikura, A;Ikeda, K;Hosaka, T.;Takada, A;Kim, H.S.;Okamoto, Y. J.
  9. J. heterocyclic Chem v.32 Kurasawa, Y.;Miyashita, R.;Takada, A.;Kim, H. S.;Okamoto, Y. J.
  10. Heterocycles v.41 Kurasawa, Y.;Takada, A;Kim, H. S.
  11. J. Heterocyclic Chem v.30 Kurasawa, Y;Kureyama, T.;Yoshishiba, N.;Okano, T.;Takada, A.;Kim, H.S.;Okamoto, Y.
  12. J. Heterocyclic Chem v.30 Kurasawa, Y;Yoshishiba, N.;Kureyama, T.;Takada, A.;Kim, H.S.;Okamoto, Y.