香豆素噻唑烷二酮类化合物的合成

Synthesis of Coumarin-thiazolidinediones

运用拼合原理并根据构效关系研究结果,设计了香豆素噻唑烷二酮类化合物,合成方法是以甲基取代的香豆素为原料,经NBS溴化后,再与5-(4-羟基苄叉)-噻唑烷-2,4-二酮在NaH作用下缩合得到,其中中间体5-(4-羟基苄叉)-噻唑烷-2,4-二酮是由噻唑烷二酮与对羟基苯甲醛在哌啶催化下缩合得到,共合成了5-[4-(香豆素-7-亚甲氧基)苄叉]-噻唑烷-2,4-二酮、5-[4-(4-甲基香豆素-7-亚甲氧基)苄叉]-噻唑烷-2,4-二酮、5-[4-(香豆素-6-亚甲氧基)苄叉]-噻唑烷-2,4-二酮、5-[4-(7-甲氧基香豆素-4-亚甲氧基)苄叉]-噻唑烷-2,4-二酮、5-[4-(3-溴香豆素-7-亚甲氧基)苄叉]-噻唑烷-2,4-二酮、5-[4-(3-溴-4-甲基香豆素-7-亚甲氧基)苄叉]-噻唑烷-2,4-二酮6个香豆素噻唑烷二酮类化合物,结构均经IR1、HNMR、MS确定,两步反应合成目标化合物总产率分别为10.4%、13.1%、7.1%、16.0%、22.0%、18.0%。

On the basis of structure -activity relationship, coumarin-thiazolidinediones were designed by matching principle. Substituted methyl-coumarins were firstly brominated by NBS, and then reacted in the presence of Nail with 5-[ （4-hydroxy）-benzylidene ] thiazolidine-2, 4-dione, which was made by condensation of thiazolidinedione with p-hydroxybenzaldehyde. Six compounds were synthesized, namely 5- E 4- （ coumarin-7-methoxy ） benzylidene ] thiazolidine-2,4-dione, 5-14- （ 4-methylcoumarin-7-methoxy ） benzylidene ] thiazolidine-2,4-dione, 5-14- （ coumarin-6-methoxy ） benzylidene ] thiazolidine-2,4-dione, 5- [4-（ 7-methoxylcoumarin-4-methoxy ） benzylidene ] thiazolidine-2, 4-dione, 5-E 4-（ 3-bromocoumarin-7- methoxy ） benzylidene ] thiazolidine-2, 4-dione, and 5-[ 4-（ 3-bromo-4-methylcoumarin-7-methoxy ） benzylidene ] thiazolidine-2,4-dione. Their structures were identified by IR, ^1HNMR and MS spectra. Total yields of the two-step reactions were respectively 10.4%, 13.1% ,7.1%, 16.0% ,22.0% and 18.0%.