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首页> 外文期刊>Chemistry: A European journal >Synthesis of aminopyridines and aminopyridones by cobalt-catalyzed [2+2+2] cycloadditions involving yne-ynamides: Scope, limitations, and mechanistic insights
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Synthesis of aminopyridines and aminopyridones by cobalt-catalyzed [2+2+2] cycloadditions involving yne-ynamides: Scope, limitations, and mechanistic insights

机译：钴催化的涉及炔炔酰胺的[2 + 2 + 2]环加成反应合成氨基吡啶和氨基吡啶酮：范围，局限性和机理见解

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摘要

An in-depth study of the cobalt-catalyzed [2+2+2] cycloaddition between yne-ynamides and nitriles to afford aminopyridines has been carried out. About 30 nitriles exhibiting a broad range of steric demand and electronic properties have been evaluated, some of which open new perspectives in metal-catalyzed arene formation. In particular, the use of [CpCo(CO)(dmfu)] (dmfu=dimethyl fumarate) as a precatalyst made possible the incorporation of electron-deficient nitriles into the pyridine core. Modification of the substitution pattern at the yne-ynamide allows the regioselectivity to be switched toward 3- or 4-aminopyridines. Application of this synthetic methodology to the construction of the aminopyridone framework using a yne-ynamide and an isocyanate was also briefly examined. DFT computations suggest that 3-aminopyridines are formed by formal [4+2] cycloaddition between the nitrile and the intermediate cobaltacyclopentadiene, whereas 4-aminopyridines arise from an insertion pathway.
机译：深入研究了乙炔基酰胺和腈之间钴催化的[2 + 2 + 2]环加成反应以提供氨基吡啶。已评估了约30个具有广泛空间需求和电子性能的腈，其中一些为金属催化的芳烃形成开辟了新的前景。特别地，使用[CpCo（CO）（dmfu）]（dmfu ＝富马酸二甲酯）作为预催化剂使得可以将缺电子的腈掺入吡啶核中。炔炔基上的取代模式的修饰使区域选择性转向3-或4-氨基吡啶。还简要地研究了该合成方法在使用炔属酰胺和异氰酸酯构建氨基吡啶酮骨架中的应用。 DFT计算表明，3-氨基吡啶是由腈和中间体钴环戊二烯之间的正式[4 + 2]环加成反应形成的，而4-氨基吡啶则来自于插入途径。

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