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| 6,7-二氢-5H-1-氮茚的合成研究 | |
| 引用本文： | 陈艳雪,赵广乐,李阳,闫喜龙,王东华,陈立功.6,7-二氢-5H-1-氮茚的合成研究[J].有机化学,2009,29(8):1223-1227. |
| 作者姓名： | 陈艳雪 赵广乐 李阳 闫喜龙 王东华 陈立功 |
| 作者单位： | 1. 天津大学化工学院,天津,300072;石家庄铁道学院材料科学与工程分院,石家庄,050043 2. 天津大学化工学院,天津,300072 3. 天津大学药物科学与技术学院,天津,300072 |
| 摘 要： | 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 Michael加成 催化环合 |
| 收稿时间： | 2008-11-26 |
| 修稿时间： | 2009-1-12 |
Synthesis of 6,7-Dihydro-5H-1-pyrindine |
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| Chen Yanxue,Zhao Guangle,Li Yang,Yan Xilong,Wang Donghua,Chen Ligong.Synthesis of 6,7-Dihydro-5H-1-pyrindine[J].Chinese Journal of Organic Chemistry,2009,29(8):1223-1227. | |
| Authors: | Chen Yanxue Zhao Guangle Li Yang Yan Xilong Wang Donghua Chen Ligong |
| Institution: | (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) |
| 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%. |
| Keywords: | 6 |
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