Cascade synthesis of 2-amino-5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole by reaction of 4-chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide with thiourea

被引：0
|
作者：
G. N. Rozentsveig
V. Yu. Serykh
K. A. Chernyshev
I. B. Rozentsveig
G. G. Levkovskaya
L. B. Krivdin
机构：
[1] Russian Academy of Sciences,Favorskii Irkutsk Institute of Chemistry, Siberian Division
来源：
Russian Journal of Organic Chemistry | 2011年 / 47卷
关键词：
Thiourea; Thiazole; Phenylethyl; Benzenesulfonamide; Thiazole Ring;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
4-Chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide reacted with thiourea on heating in DMF in the presence of sodium carbonate to give 5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole-2-amine. A probable reaction scheme includes cyclization of the initial N-dichloroethyl amide to N-sulfonyl-2,3-diaryl-2-chloroaziridine which undergoes isomerization with opening of the three-membered ring to 1-arylsulfonylamino-2-chloro-2-(4-methoxyphenyl)-1-phenylethene. The subsequent heterocyclization in the reaction with thiourea is accompanied by aromatization via elimination of the arenesulfonamide fragment.
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