Copper-Catalyzed CNH2 Arylation of 2-Aminobenzimidazoles and Related C-Amino-NH-azoles
Copper-Catalyzed CNH2 Arylation of 2-Aminobenzimidazoles and Related C-Amino-NH-azoles
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DOI：
10.1002/adsc.201600035
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发表时间：
2016-06-30
影响因子：
5.4
通讯作者：
Das, Parthasarathi
中科院分区：
文献类型：
--
作者：
Rao, Desaboini Nageswar;Rasheed, Sk.;Das, Parthasarathi
在 60 ℃、露天条件下，在 2,2-联吡啶和碳酸铯存在下，实现了铜 (II) 催化的 2-氨基苯并咪唑和相关的 C-氨基-NH-唑的选择性 CNH2 芳基化，这是在其他反应性亲核位点存在下铜催化选择性 CNH2 芳基化的第一个方法。获得了先前未开发的具有多个亲核位点的杂芳族化合物，这些位点在 CNH2 位点选择性芳基化，为快速递送多种具有药用价值的氨基唑 CNH（芳基）衍生物提供了一种特殊的工具，而无需对环 NH 键进行任何保护/脱保护。这是5-氨基吲唑、4-氨基吡唑、5-氨基吡唑、9H-嘌呤-6-胺和1H-吡唑并[3,4-d]嘧啶-4-胺衍生物的选择性CNH2芳基化的第一个例子。
A copper(II)-catalyzed selective CNH2 arylation of 2-aminobenzimidazoles and related C-amino-NH-azoles was achieved in presence of 2,2-bipyridine and cesium carbonate at 60 degrees C under open air conditions and this is first method for the copper-catalyzed selective CNH2 arylation in the presence of other reactive nucleophilic sites. Previously unexplored heteroaromatics possessing multiple nucleophilic sites that are selectively arylated at the CNH2 position are obtained, providing an exceptional tool for rapid delivery of a diverse array of medicinally important CNH(aryl) derivatives of aminoazoles without any protection/deprotection of ring NH bonds. It is first example for the selective CNH2 arylation of 5-aminoindazole, 4-aminopyrazole, 5-aminopyrazole, 9H-purine-6-amine, and 1H-pyrazolo[3,4-d]pyrimidin-4-amine derivatives.