New Synthesis of 4-(1-Adamantyl)-2-aryl-1,3-thiazoles from 4-(1-Adamantyl)-1,2,3-thiadiazole

被引：2
|
作者：
Shchipalkin, A. A. [1 ]
Petrov, M. L. [1 ]
Kuznetsov, V. A. [1 ]
机构：
[1] St Petersburg State Inst Technol, St Petersburg 190013, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 47卷 / 12期
基金：
俄罗斯基础研究基金会;
关键词：
Thiazole; Thiadiazole; Ethynyl; Oxoethyl; Anhydrous Tetrahydrofuran;
D O I：
10.1134/S1070428011120165
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of 4-(1-adamantyl)-1,2,3-thiadiazole with potassium tert-butoxide generated potassium 2-(1-adamantyl)ethynethiolate which reacted with aromatic carboxylic acid chlorides to give unstable S-[2-(1-adamantyl)ethynyl] arenecarbothioates whose acid hydrolysis afforded S-[ 2-(1-adamantyl)-2-oxoethyl] arenecarbothioates. The latter reacted with ammonium acetate in acetic acid yielding 4-(1-adamantyl)-2-aryl-1,3-thiadiazoles. Reactions of 4-(1-adamantyl)-2-(4-chloro-3-nitrophenyl)-1,3-thiadiazole with cyclic secondary amines gave the corresponding products of nucleophilic replacement of the chlorine atom in the aromatic ring.
引用
收藏
页码：1878 / 1881
页数：4
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