碘催化合成四氢喹啉衍生物的合成研究

Study on Synthesis of Tetrahydroquinolines Catalyzed by Iodine

研究了在碘催化下芳基亚胺与二氢吡喃的反应,以较高的产率获得了预期的四氢喹啉产物。详细考察了催化剂的用量、溶剂的选择对该反应的影响。结果表明,催化剂碘的用量对反应的影响明显,用量达到15mmol%时,产率最高,催化效果最好;反应溶剂对反应的影响不大,相比之下在CH2Cl2中的效果最好。"一锅法"反应结果表明,碘也能够直接催化芳香醛、苯胺、二氢吡喃的三组分反应,获得的化学产率与使用预制的N-芳基亚胺相当。所得化合物经1 H NMR、13 C NMR测试技术进行表征。

Iodine was found to be an efficient catalyst for the reaction of arylimine with dihydropyran to provide tetrahydroquinolines in good yield.The influence of the loading of iodine and solvents on the＂one pot＂reaction was studied.The amount of iodine played an important role for the yield of the reaction,and the results showed that adding 15mmol%iodine was gave an excellent yield and very good catalytic activity.The solvent effect in the reaction was not obvious,and by comparison dichloromethane was preferred.One pot synthesis of tetrahydroqinolines from aryl aldehyde,aniline and dihydropyran was also achieved using iodine as the catalyst,The yield of the＂one pot＂reaction was comparable with that obtained using Narylimine.The obtained compounds were characterized by 1 HNMR and 13 C NMR.