多取代1,4-戊二烯-3-醇的合成及其在螺环四氢喹啉衍生物合成中的应用

摘要

以取代邻氨基苯甲酸为起始原料,经6步反应合成了7个多取代1,4-戊二烯-3-醇(7a~7g);以7a~7g为原料,5 mol%FeCl3为催化剂,CH2Cl2为溶剂,于室温反应合成了7个螺环四氢喹啉衍生物(8a~8g),其结构经1H NMR, 13C NMR, IR和HR-MS(ESI)表征.采用X-射线单晶衍射研究了8d的晶体结构.结果表明:8d的晶胞参数a=14.001(3) , b=12.335(2) , c=11.587(3) , α=90°, β=95.497(2)°, γ=90°, V=1 991.9(7) 3, Z=4, μ=0.182 mm-1, F(000)=816.0, R[F2>2σ(F2)]=0.053 7, wR(F2)=0.132 5.%Seven multi-substituted 1,4-pentadiene-3-ols(7a~7g) were synthesized by a six-step reaction from substituted anthranilic acids.Seven spiro-tetrahydroquinoline compounds(8a~8g) were synthesized from 7a~7g, using 5 mol%FeCl3 as the catalyst and CH2Cl2 as solvent at rt.The structures were characterized by 1H NMR, 13C NMR, IR and HR-MS(ESI).The crystal structure of 8d was investigated by X-ray single crystal diffraction.The results indicated that the crystal parameters of 8d were a=14.001(3) , b=12.335(2) , c=11.587(3) , α=90°, β=95.497(2)°, γ=90°, V=1 991.9(7) 3, Z=4, μ=0.182 mm-1, F(000)=816.0, R[F2>2σ(F2)]=0.053 7, wR(F2)=0.132 5.