Studies On Synthesis Of Novel Indolin-2-ones Derivatives Containing Thiazole

Indole dione compounds and thiazole compounds are favored by many scientific research workers heterocyclic compounds,medical drugs in the field of many bio-active drug molecules are the existence of these two structures,with these two groups The compounds of the compounds generally have good biological activity,such as antifungal,anti-cancer,anti-tumor,antidepressant and anti-inflammatory.In this paper,a series of novel derivatives containing thiazolylindol-2-one were designed and synthesized.The structures of the compounds were characterized by IR,MS,~1HNMR and 13 CNMR.The main results of this study are as follows:Firstly,The indole dione is reacted with the substituted benzyl chloride using an improved method to form the intermediate 1-substituted-indole-2,3-dione 1,than,The intermediate 1-substituted-indole-2,3-dione 1 is reacted with thiosemicarbazide to form the intermediate 1-substituted-indole-2,3-dione thiosemicarbazone 2.Secondly,Using the synthesized intermediate product 1-substituted-indole-2,3-dione thiosemicarbazone 2 and 2-bromoacetophenone in the presence of glacial acetic acid as the catalyst to give the desired product 1-substituted-3-(5-phenylthiazol-2-yl)hydrazonoindol-2-one 3,Finally,the synthesis method was optimized,and the optimum conditions were obtained as follows: the ratio of the intermediate product 2 to the 2-bromoacetophenone was 1;1.3,C2H5 OH was the solvent,the temperature of the system was 60 ?,the whole process was 5.5h,The catalyst is glacial acetic acid..Thirdly,The intermediate product 1-substituted-indole-2,3-dione thiosemicarbazone 2 and 2-chloroacetoacetate were reacted under the conditions of glacial acetic acid as the catalyst to give the target product 1-substituted-3-(4-methyl-5-ethoxyformacylthiazol-2-yl)hydrazonoindol-2-one 4,Finally,the synthesis method was optimized,and the optimum synthesis conditions were obtained.When the ratio of intermediate 2 to ethyl 2-chloroacetoacetate was 1;1.3,C2H5 OH was solvent,the temperature of the system was 70 ?,the whole process was 6.5h,the catalyst was glacial acetic acid.