Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

A Selective Synthesis of Isoxazolo[2,3-${\alpha}$]quinoxalines and Pyrrolo[1,2-${\alpha}$]quinoxalines by 1,3-Dipolar Cycloaddition Reaction

1,3-쌍극성 고리화 첨가반응에 의한 Isoxazolo[2,3-${\alpha}$]quinoxaline류와 Pyrrolo[1,2-${\alpha}$]quinoxaline류의 선택적인 합성

  • Kim Ho Sik (Department of Chemistry, Teacher's College, Hyosung Women's University) ;
  • Nam Soon Hwa (Department of Chemistry, Teacher's College, Hyosung Women's University) ;
  • Kurasawa Yoshihisa (School of Pharmaceutical Sciences, Kitasato University)
  • 김호식 (曉星女子大學校 師範大學 化學科) ;
  • 남순화 (曉星女子大學校 師範大學 化學科) ;
  • Published : 19900900
Download PDF
⟨ Previous Next ⟩

Abstract

The reaction of 2,6-dichloroquinoxaline (13) with m-chloroperbenzoic acid gave 2,6-dichloroquinoxaline 4-oxide (14), whose reaction with pyrrolidine or indoline provided 2-substituted 6-chloroquinoxaline 4-oxides (15). The isoxazolo[2,3-a]quinoxalines (16) and pyrrolo[1,2-a]quinoxalines (17) were selectively synthesized from the 2-substituted 6-chloroquinoxaline 4-oxides (15) and dimethyl acetylenedicarboxylate. Moreover, the pyrrolo[1,2-a]quinoxalines (17) were found to be produced by the ring transformation of the isoxazolo[2,3-a]quinoxalines (16).

2,6-dichloroquinoxaline (13)과 m-chloroperbenzoic acid를 반응시켜 2,6-dichloroquinoxaline 4-oxide (14)를 합성하고, 이것과 pyrrolidine 혹은 indoline을 반응시켜 2-substituted 6-chloroquinoxaline 4-oxide류(15)를 합성하였다. 그리고 이들과 dimethyl acetylenedicarboxylate를 반응시키니 isoxazolo[2,3-a]quinoxaline류(16)와 pyrrolo[1,2-a]quinoxaline류 (17)가 선택적으로 합성되었다. 더욱이 pyrrolo[1,2-a]quinoxaline류 (17)는 isoxazolo[2,3-a]quinoxaline류 (16)의 고리변환에 의하여 생성된다는 것을 알았다.

Keywords

References

  1. A part of this work was reported in the 20th Congress of Heterocyclic Chemistry
  2. U. S. Patent, 3, 692, 633 E. P. Stapley;J. M. Mata;F. G. Wolf;T. W. Miller
  3. U. S. Patent, 3, 479, 354 R. H. B. Galt
  4. J. Heterocyclic Chem. v.21 P. Devi;J. S. Sandhu
  5. Synthesis M. Hasegawa;T. Takabatake
  6. Antimicrob. Agents and Chemother J. R. Valenta;J. R. E. Hoover;J. F. Pagano
  7. Synthesis K. Ley;F. Seng
  8. Chem. Abstr. E. P. Stapley;J. M. Mata;F. G. Wolf;T. W. Miller
  9. Pol. Patent, 69, 644 A. Zmujdzin
  10. Chem. Abstr. v.60 D. W. J. Lane;G. T. Newbold
  11. Bri. Patent, 1, 041, 011 D. W. J. Lane;G. T. Newbold
  12. Angew. Chem. v.72 K. Sasse;R. Wegler;G. Unterstenhoefer;F. Grewe
  13. Annu. Rept. Brit. Empire Cancer Campaign C. W. Rees;J. A. Waite
  14. Jap. Patent, 17747 T. Miyagi;H. Yamamoto
  15. U. S. Patent, 3, 674, 793 Q. S. Soper
  16. Chem. Abstr. v.77 Q. S. Soper
  17. Yakugaku Kenkyo v.30 S. Numada;N. Watanabe;K. Yamamoto;H. Zenno
  18. Chem. Abstr. v.53 S. Numada;N. Watanabe;K. Yamamoto;H. Zenno
  19. Angew. Chem. Internat. Edit. v.3 K. G. Kleb;E. Siegel;K. sasse
  20. The Chemistry of Hetercyclic Compounds. Condensed Pyrazines C. W. H. Cheeseman;R. F. Cookson;A. Weissberger(ed.);E. C. Taylor(ed.)
  21. J. Korean Chem. Soc. v.30 J. D. Kim;H. S. Kim;S. W. Han
  22. J. Korean Chem. Soc. v.31 J. D. Kim;H. S. Kim;S. W. Han
  23. Chem. Abstr. v.81 A. Zmujdzin
  24. J. Korean Chem. Soc. v.33 H. S. Kim;S. W. Han;J. D. Kim
  25. J. Korean Chem. Soc. v.34 I. Y. Kang;S. Y. Kim;H. S. Kim;J. D. Kim;K. Huh
  26. Yakhak Hoeji v.34 I. Y. Kang;S. Y. Kim;H. S. Kim;K. Huh
  27. J. Heterocyclic Chem. v.26 Y. Kurasawa;Y. Kamigaki;H. S. Kim;R. Futatsukawa;M. Kanoh;M. Okiyama;A. Takada;Y. Okamoto
  28. J. Heterocyclic Chem. v.26 Y .Kurasawa;H. S. Kim;K. Yonekura;A. Takada;Y. Okamoto
  29. J. Heterocyclic Chem. v.26 Y. Kurasawa;Y. Kamigaki;H. S. Kim;K. Yonekura;A. Takada;Y. Okamoto
  30. J. Heterocyclic Chem. v.26 Y. Kurasawa;Y. Kamigaki;H. S. Kim;C. Watanabe;M. Kanoh;M. Okiyama;A. Takada;Y. Okamoto
  31. J. Heterocyclic Chem. v.26 H. S. Kim;Y. Kurasawa;A. Takada
  32. J. Heterocyclic Chem. v.26 H. S. Kim;Y. Kurasawa;A. Takada
  33. J. Heterocyclic Chem. v.26 Y. kurasawa;H. S. Kim;R. Futatsukawa;C. Watanabe;A. Takada;Y. Okamoto
  34. J. Heterocyclic Chem. v.17 S. Kano;S. Shibuya;Y. Yuasa
  35. J. Heterocyclic Chem. v.26 H. S. Kim;Y. Kurasawa;A. Takada
  36. J. Heterocyclic Chem. v.27 H. S. Kim;Y. Kurasawa;C. Yoshii;M. Masuyama;A. Takada;Y. Okamoto
  37. J. Heterocyclic Chem. H. S. Kim;Y. Kurasawa;C. Yoshii;M. Masuyama;A. Takada;Y. Okamoto
  38. Heterocycles v.23 K. Makino;G. Sakata;K. Morimoto;Y. Ochiai
  39. Chem. Abstr. v.82 M. Ungureanu;I. Druta;I. Zugravescu
  40. An. Stiint. Univ. v.20 M. Ungureanu;I. Druta;I. Zugravescu
  41. J. Chem. Soc. Chem. Commun. J. C. Mason;G. Tennant
  42. Tetrahedron Lett. A. R. Gagneux;R. Goeschke
  43. J. Am. Chem. Soc. v.90 J. E. Baldwin;R. G. Pudussery;A. K. Quresh;B. Sklarz
  44. Tetrahedron Lett. I. Adachi;K. Harada;H. Kano
  45. J. Chem. Soc. G. Tennant
  46. 1,3-Dipolar Cycloaddition Chemistry v.II A. Padwa;E. C. Taylor(ed.);A. Weissberger(ed.)
  47. Tetrahedron v.20 Y. Ahmad;M. S. habib;Ziauddin
  48. J. Heterocyclic Chem. v.7 R. Y. Ning;G. F. Field;L. H. Sternback
  49. J. Org. Chem. v.36 A. Walser;G. Silverman;R. I. Fryer;L. H. Sternbach
  50. J. Org. Chem. v.35 E. Abushanab