From imidates to vinyl-1,2,4-triazoles: Synthesis, mechanistic aspects and first issues of their reactivity
From imidates to vinyl-1,2,4-triazoles: Synthesis, mechanistic aspects and first issues of their reactivity
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DOI：
10.1016/j.tet.2018.10.050
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发表时间：
2018-12-06
期刊：
影响因子：
2.1
通讯作者：
Prim, Damien
中科院分区：
文献类型：
--
作者：
Azzouni, Safa;Abdelli, Abderrahmen;Prim, Damien
各种取代的酰亚胺酯与肼衍生物的反应代表了一种有效且易于设置的合成5-乙烯基-1，2，4-三唑衍生物的入口。三唑环的结构允许在五元杂环的N（1）、C（3）和C（5）位置以良好至高产率安装各种取代基组合。该方法揭示了对5-乙烯基-1，2，4-三唑的选择性，避免了潜在的七元和五元副产物的形成，理论计算和NMR实验支持。最后描述了Pd催化的乙烯基片段芳基化为5-苯乙烯基-1，2，4-三唑和Cu催化的N（1）位芳基化的第一线。(C)2018爱思唯尔有限公司版权所有
The reaction of variously substituted acylimidates with hydrazine derivatives represents an efficient and easy to set synthetic entry towards 5-vinyl-1,2,4-triazole derivatives. The construction of the triazole ring allows the installation of variety of substituent combination at the N(1), C(3) and C(5) positions of the five-membered heterocycle in good to high yields. The method reveals selective towards 5-vinyl-1,2,4-triazoles avoiding the potential formation of seven- and five-membered side-products as supported by theoretical calculations and NMR experiments. First lines of Pd-catalyzed arylation of the vinyl fragment towards 5-styryl-1,2,4-triazoles and Cu-catalyzed arylation at the N(1) site are finally described. (C) 2018 Elsevier Ltd. All rights reserved.