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

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (08): 1223-1227. Previous Articles Next Articles

Original Articles

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

(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

(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

Abstract

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

Cite this article

Chen, Yanxue ^a,b ; Zhao, Guangle ^a; Li, Yang ^a; Yan, Xilong ^a;
Wang, Donghua ^c; Chen, Ligong^*,a
. Synthesis of 6,7-Dihydro-5H-1-pyrindine[J]. Chin. J. Org. Chem., 2009, 29(08): 1223-1227.

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6,7-二氢-5H-1-氮茚的合成研究

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

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