Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

Synthesis of Novel 1,2-Diazepino[3,4-b]quinoxaline and Pyridazino[3,4-b]quinoxaline Derivatives

새로운 1,2-Diazepino[3,4-b]quinoxaline과 Pyridazino[3,4-b]quinoxaline

  • Kim, Ho Sik (Department of Chemistry, Catolic University of Taegu-Hyosung) ;
  • Jeong, Geuk (Department of Industrial Chemistry, Ulsan College)
  • 김호식 (대구효성가톨릭대학교 자연대 화학과) ;
  • 정극 (울산과학대학 공업화학과)
  • Published : 19990600
Download PDF
⟨ Previous Next ⟩

Abstract

The 1,3-dipolar cycloaddition reaction of the quinoxaline 4-oxide 10 with 2-chloroacrylonitrile gave the 2,3-dihydro-lH-1,2-diazepino[3,4-blquinoxalines lla, b, respectively, which were converted into the 2,3,4,6-tetrahydro-lH-l,2-diazepino[3,4-b]quinoxaline 12. The reaction of compound lla with selenium dioxide in acetic acid/water resulted in ring transformation to give the 1,4-dihydro-4-oxopyridazino[3,4-blquinoxaline 13.

Quinoxaline 4-oxide 10을 2-chloroacrylonitrile과 반응시켜 1,3-쌍극성 고리화 첨가반응으로 2,3-dihydro-1H-1,2-diazepino[3,4-b]quinoxaline류 11a, b를 합성하였고, 이들을 2,3,4,6-tetrahydro-1H-1,2-diazepino-[3,4-b]quinoxaline 12로 변환시켰다. 그리고 ??嵐?11a를 아세트산/물 용매에서 SeO2와 반응시켜서 고리변환에 의해 1,4-dihydro-4-oxopyridazino[3,4-b]quinoxaline 13을 합성하였다.

Keywords

References

  1. Comprehensive Heterocyclic Chemistry Ⅱ v.9 Katritzky, A. R.;Rees, C. W.;Scriven, E. F. V.;Read, R. W.(Ed.)
  2. Comprehensive Heterocyclic Chemistry Ⅱ v.6 Katritzky, A. R.;Rees, C. W.;Scriven, E. F. V.;Coates, W. J.(Ed.)
  3. The Chemistry of Heterocyclic Compounds. Condensed Pyrazines Cheeseman, C. W. H.;Cookson, R. F.;Weissberger, A.(Eds.);Taylor, E. C.(Eds.)
  4. J. Heterocyclic Chem. v.32 Kurasawa, Y.;Takada, A;Kim, H. S.
  5. 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.
  6. J. Heterocyclic Chem. v.34 KIm, H. S.;Kim. E. K.;Kim. S. S.;Park, Y. T.;Hong, Y. S.;Kurasawa, Y.
  7. J. Heterocyclic Chem. v.34 Kim, H. S.;Kim, T. E.;Kwag, S. T.;Park, Y. T.;Hong, Y. S.;Kurasawa, Y.
  8. J. Heterocyclic Chem. v.35 Kim, H. S.;Kim. E. A;Jeong, G.;Park, Y. T.;Hong, Y. S.;Okamoto, Y.;Kurasawa, Y.
  9. J. Heterocyclic Chem. v.35 Kim, H. S.;Kim, E. A.;Lee, S. U.;Kim, D. I.;Han, S. W.;Okamoto, Y.;Mitomi, T.;Kurasawa, Y.
  10. J. Heterocyclic Chem. v.26 Kim, H. S.;Kurasawa, Y.;Takada, A.
  11. J. Heterocyclic Chem. v.35 Kurasawa, Y.;Kim, H. S.
  12. Synthetic Commun. v.21 Pillai, P. M.;Bhat, V. S.
  13. J. Heterocyclic Chem. v.33 Ueda, T.;Asahi, M.;Nagai, S.;Sakakibara, J.
  14. J. Am. Chem. Soc. v.81 Moore, J. A.;Medeiros, R. W.
  15. J. Org. Chem. v.31 Moore, J. A.;Medeiros, R. W.;Williams, R. L.
  16. J. Am. Chem. Soc. v.81 Moore, J. A.;Binkert, J.
  17. J. Org. Chem. v.31 Wineholt, R. L.;Wyss, E.;Moore, J. A.
  18. J. Am. Chem. Soc. v.77 Moore, J. A.
  19. J. Org. Chem. v.29 Moore, J. A.;Zoll. E. C.
  20. J. Org. Chem. v.29 Bly, R. K.;Zoll. E. C.;Moore, J. A.
  21. J. Org. Chem. v.30 Moore. J. A.;Theuer, W. J.
  22. J. Chem. Soc., Chem. Commun. Amiet, R. G.;Johns, R. B.;Makham, K. R.
  23. Aust. J. Chem. v.21 Amiet, R. G.;Johns, R. B.
  24. J. Am. Chem. Soc. v.74 Gill, N. S.;James, K. B.;Lions. F.;Potts, K. T.
  25. Chem. Ber. v.38 Woelbling, H.
  26. J. Org. Chem. v.26 Halford, J. O.;Raiford, R. W.;Wissmann, G.
  27. Chem. Ber. v.95 Schmitz, E.;Ohme, R.
  28. Chem. Ber. v.38 Lieck, A.