Chinese Journal of Organic Chemistry >
One-Step Synthesis of 2,4-Disubstituted Thiazoles in Au(I) Complex/Zinc Salt Catalytic System
Received date: 2015-05-29
Revised date: 2015-08-27
Online published: 2015-09-06
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21003073, 21203093), the Natural Science Foundation of Jiangsu Province (No. BK20141388) and the Qing Lan Project of Jiangsu Province.
Ten typical P,N-bidentate ligands were selected to synthesize the corresponding Au(I) complexes. The catalytic system of Au(I) complex/metal salt was employed in the catalytic oxidation of terminal alkynes with the oxidant of 8-methylquinoline N-oxide. And then 2,4-disubstituted thiazoles were synthesized from the oxidized alkynes and thioamides. It was found that the catalytic system of 5 mol% Mor-DalPhosAuCl/10 mol% Zn(NTf2)2 showed the optimum catalytic performance in this reaction via adjusting reaction parameters. Furthermore, ten kinds of 2,4-disubstituted thiazoles were effectively synthesized in one-step. So a simple and direct synthetic route was explored for the preparation of thiazoles and their derivatives.
Key words： Au(I) complex; 8-methylquinoline N-oxide; terminal alkyne; thioamide; thiazole
Wu Gongde , Wang Xiaoli , Zhang Liming , Zhang Fang , Liu Xianfeng , Liu Congrong . One-Step Synthesis of 2,4-Disubstituted Thiazoles in Au(I) Complex/Zinc Salt Catalytic System[J]. Chinese Journal of Organic Chemistry, 2015 , 35(12) : 2537 -2544 . DOI: 10.6023/cjoc201505046
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