Substitution Reactions of Cyanopyridines with Organometallics

유기금속화합물에 의한 Cyanopyridines의 치환반응에 관한 연구

  • Kim, Jung-Gyun (Department of Chemistry, Pusan National University) ;
  • Yu, Dong-Sik (Department of Chemistry, Pusan National University) ;
  • Moon, Sung-Hwan (Department of Chemistry, Pusan National University) ;
  • Park, Jin-Il (Department of Chemistry, Pusan National University) ;
  • Park, Won-Woo (Department of Chemistry, Pusan National University)
  • 김정균 (부산대학교 자연과학대학 화학과) ;
  • 유동식 (부산대학교 자연과학대학 화학과) ;
  • 문성환 (부산대학교 자연과학대학 화학과) ;
  • 박진일 (부산대학교 자연과학대학 화학과) ;
  • 박원우 (부산대학교 자연과학대학 화학과)
  • Published : 1993.09.20

Abstract

3-Cyanopyridine, when treated with organolithium or Grignard reagents, gives addition to the 6-position and provides a series of 2-substituted 5-cyanopyridines (6-substituted 3-cyanopyridines). Alternatively, 2-and 4-cyanopyridine react with $CH_3Li$ or $CH_3Mgl$ and provide 2-acetylpyridine and 4-acetylpyridine, respectively.

3-Cyanopyridine을 organolithium 나 Grignard 시약과 반응시키면 6-위치에 첨가반응이 일어나 2-치환된 5-cyanopyridine류(6-치환된 3-cyanopyridine류)가 합성되었다. 반면, 2- 또는 4-cyanopyridine을 $CH_3Li$이나 $CH_3Mgl$와 반응시키면, 각각 2-acetylpyridine과 4-acetylpyridine이 합성되었다.

Keywords

References

  1. J. Org. Chem. v.56 P. R. Sleath;A. L. Handlon;N. J. Oppenheimer
  2. Angew. Chem. Int. Ed. Eng. v.30 R. Amann;D. Spitzner
  3. J. Org. Chem. v.56 J. Barluenga;F. J. Gonzalez;R. P. Carlon
  4. Nucleosides and Nucleotides v.10 no.1-3 P. E. Joos;E. L. Esmans;R. A. Domminsse;J. A. Lepoivre;F. C. Alderweireldt
  5. J. Chem. Soc. Perkin Trans. I J. Kobayashi;T. Murayama;S. Kosuge;F. Kanda;M. Ishibashi;H. Kobayashi;Y. Ohizumi;T. Ohta;S. Nozoe
  6. J. Med. Chem. v.15 J. G. Cannon;J. C. Kim;M. A. Aleem
  7. J. Med. Chem. v.23 J. G. Cannon;T. Lee;H. D. Goldman
  8. Heteroaromatic Nitrogen Compounds. Pyrroles and Pyridines K. Schofield
  9. J. Org. Chem. v.42 W. E. Parhams;R. M. Piccirilli
  10. Comprehensive Organic Synthesis v.4 Paradisi;B. M. Trost(ed.);I. Fleming(ed.)
  11. J. Org. Chem. v.47 A. I. Meyers;R. A. Gabel
  12. Tetrahedron v.41 M. Reuman;A. I. Meyers
  13. J. Am. Chem. Soc. v.70 R. L. Frank;C. Weatherbee
  14. Chem. Communi. C. S. Giam;J. L. Stout
  15. J. Chem. Soc. Perkin Trans. I S. G. Davies;M. R. Shipton
  16. J. Org. Chem. v.39 R. F. Francis;W. Davis;J. T. Wisener
  17. Chem. Communi. R. F. Francis;J. T. Wisener;J. M. Paul
  18. J. Chem. Soc. Perkin Trans. I D. Bryce-Smith;P. J. Morris;B. J. Wakefield