有机化学 ›› 2014, Vol. 34 ›› Issue (6): 1161-1166.DOI: 10.6023/cjoc201312024 上一篇    下一篇

研究论文

1-(2-吡啶基)-2-氮杂-1, 3-丁二烯的合成与应用

杨维芳, 徐晓丽, 张站斌   

  1. 北京师范大学化学学院 北京 100875
  • 收稿日期:2013-12-19 修回日期:2014-02-06 发布日期:2014-02-21
  • 通讯作者: 张站斌 E-mail:zhangzb@bnu.edu.cn

Synthesis and Application of 1-(Pyridin-2-yl)-2-azabuta-1, 3-dienes

Yang Weifang, Xu Xiaoli, Zhang Zhanbin   

  1. College of Chemistry, Beijing Normal University, Beijing 100875
  • Received:2013-12-19 Revised:2014-02-06 Published:2014-02-21

以2-吡啶甲醛为起始原料制备1-(2-吡啶基)-2-氮杂-1,3-丁二烯(2),然后与烯烃、炔烃发生Diels-Alder反应分别得到6-(2-吡啶基)-2-哌啶酮和6-(2-吡啶基)-二氢-2-吡啶酮. 用2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)氧化 6-(2-吡啶基)-二氢-2-吡啶酮得到6-(2-吡啶基)-2-吡啶酮,最后用三氯氧磷处理得到联吡啶类化合物.

关键词: 2-氮杂-1,3-丁二烯, Diels-Alder反应, 2-哌啶酮, 2-吡啶酮

1-(Pyridin-2-yl)-2-azabuta-1,3-dienes (2) prepared from pyridine-2-carboxaldehyde underwent Diels-Alder reaction with electron-poor dienophiles such as alkenes and alkynes to give 6-(pyridin-2-yl)piperidin-2-ones and dihydro-6-(pyri- din-2-yl)pyridin-2-ones. Dihydro-6-(pyridin-2-yl)pyridin-2-one was oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to afford 6-(pyridin-2-yl) pyridin-2-one. Treatment of 6-(pyridin-2-yl)pyridin-2-one with phosphorus oxychloride gave bipyridine derivative.

Key words: 2-azabuta-1,3-diene, Diels-Alder reaction, piperidin-2-one, pyridin-2-one