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有机化学 ›› 2009, Vol. 29 ›› Issue (08): 1223-1227. 上一篇    下一篇

研究论文

6,7-二氢-5H-1-氮茚的合成研究

陈艳雪a,b; 赵广乐a ; 李 阳a ; 闫喜龙a ; 王东华c ; 陈立功*,a   

  1. (a天津大学化工学院 天津 300072)
    (b天津大学药物科学与技术学院 天津 300072)
    (c石家庄铁道学院材料科学与工程分院 石家庄 050043)
  • 收稿日期:2008-11-26 修回日期:2009-01-12 发布日期:2009-08-30
  • 通讯作者: 陈立功

Synthesis of 6,7-Dihydro-5H-1-pyrindine

Chen, Yanxue a,b ; Zhao, Guangle a; Li, Yang a; Yan, Xilong a;
Wang, Donghua c; Chen, Ligong*,a
  

  1. (a School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072) (b School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072) (c School of Material Science and Engineering, Shijiazhuang Railway Institute, Shijiazhuang 050043)
  • Received:2008-11-26 Revised:2009-01-12 Published:2009-08-30
  • Contact: Chen, Ligong

PDF

1899

被引次数

9 | 2

以价廉易得的己二酸二甲酯为原料, 在甲醇钠的催化下, 通过Dieckmann缩合反应得到2-氧代环戊烷羧酸甲酯, 收率82.2%; 2-氧代环戊烷羧酸甲酯再与丙烯腈在40%(质量比)苄基三甲基氢氧化铵甲醇溶液存在下, 经Michael加成制得1-(2-氰乙基)-2-氧代环戊烷羧酸甲酯, 收率82.5%; 进一步酸性脱羧得到3-(2-氧代环戊基)丙腈, 收率84.0%; 将脱羧产物通入装有Ni-Cu/γ-Al2O3催化剂的固定床反应器中, 催化环合最终得到6,7-二氢-5H-1-氮茚, 反应总收率33.8%.

关键词: 6,7-二氢-5H-1-氮茚, Dieckmann缩合, 催化环合, Michael加成

Methyl 2-oxocyclopentanecarboxylate was obtained via Dieckmann condensation from dimethyl adipate in 82.2% yield. Then the condensation product was reacted with acrylonitrile, in the presence of Triton B giving methyl 1-(2-cyanoethyl)-2-oxocyclopentane-carboxylate in 82.5% yield. 3-(2-Oxocyclopentyl)- propanenitrile was synthesized from methyl 1-(2-cyanoethyl)-2-oxocyclopentane-carboxylate by hydrolysis which was converted to the target molecule, 6,7-dihydro-5H-1-pyrindine, directly by reductive cyclization and aromatization in one step in the presence of Ni-Cu/γ-Al2O3. The total yield was 33.8%.

Key words: Michael addition, catalytic cyclization
, Dieckmann condensation, 6,7-dihydro-5H-1-pyrindine