四氢异喹啉衍生物的合成研究Synthesisof1234.PDF

2011 年第 31 卷 有 机 化 学 Vol. 31, 2011 第 7 期, 1087～1090 Chinese Journal of Organic Chemistry No. 7, 1087～1090 ·研究简报· 四氢异喹啉衍生物的合成研究 冯志强*,a 杨晓莉 a 叶原丰 a 郝凌云 a 胡金刚 b (a 金陵科技学院材料工程学院 南京 211169) (b 东南大学化学化工学院 南京 211189) 摘要 以间甲氧基苯乙胺和氯甲酸乙酯为原料, 通过亲核取代、关环、铝锂氢还原、脱甲基以及在 N 位上 Boc 保护 及脱保护等 9 步反应得到一系列重要的 1,2,3,4-四氢异喹啉及其衍生物. 产物的结构经核磁共振氢谱、红外光谱及元素 分析确证. 与传统四氢异喹啉衍生物的合成工艺相比, 该工艺反应条件温和、简便、经济、产率高且对环境友好. 关键词 间甲氧基苯乙胺; 1,2,3,4-四氢异喹啉; 关环 Synthesis of 1,2,3,4-Tetrahydroisoquinoline Derivatives Feng, Zhiqiang*,a Yang, Xiaolia Ye, Yuanfenga Hao, Lingyuna Hu, Jingangb a ( School of Material Engineering, Jinling Institute of Technology, Nanjing 211169) (b School of Chemistry Chemical Engineering, Southeast University, Nanjing 211189) Abstract A series of important 1,2,3,4-tetrahydroisoquinoline derivatives were synthesized from 2-(3-methoxyphenyl)ethylamine and ethyl chloroformate by nucleophilic substitution, cyclization, LiAlH4 reduction and other reactions amounting to 9 steps. The structures of the products were characterized by IR, 1 H NMR spectra and elemental analysis. Compared to the traditional synthetic procedures of tetrahydro- isoquinoline, our procedures were temperate, convenient, economical, high-yielding and environment- friendly. Keywords 2-(3-methoxyphenyl)ethylamine; 1,2,3,4-tetrahydroisoquinoline; cyclization 喹啉及其衍生物广泛存在于多种天然产物中, 很多 上腺素受体和钙通道都有较大影响[9],