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Base-mediated selective synthesis of diversely substituted N-heterocyclic enamines and enaminones by the hydroamination of alkynes

机译:通过炔烃的加氢胺进行碱介导的不同取代的N-杂环烯胺和烯胺酮的选择性合成

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摘要

Regio- and stereoselective alkynylation of various N-heterocycles 1a-l using potassium and cesium salts in DMSO is described. Terminal alkynes 2a-k and internal alkynes 4a-f provided the kinetically stable Z-enamines 3a-l and 5a-i in good to excellent yields using KOH at 120 °C. Addition of heterocyclic amines to 1,3- and 1,4-diethynylbenzene 6a-b provided the mixture of E/Z isomers with KOH; however, with Cs _2CO _3 selectively Z-isomers 7ab-db were obtained by the hydroamination at one triple bond. This developed methodology also provides an easy and novel access for the synthesis of enaminones 10a-c. The detailed work also supports the formation of cis-isomer by preferential addition of o-haloarylalkynes followed by intramolecular C2 arylation in the copper-catalyzed tandem synthesis of indolo and pyrrolo[2,1-a]isoquinolines.
机译:描述了在DMSO中使用钾盐和铯盐对各种N-杂环1a-1的区域和立体选择性炔基化。使用120℃的KOH,末端炔烃2a-k和内部炔烃4a-f提供了动力学稳定的Z-烯胺3a-1和5a-1。将杂环胺加到1,3-和1,4-二乙炔基苯6a-b中得到E / Z异构体与KOH的混合物。然而,通过Cs _2CO _3选择性地通过一个三键的加氢胺化获得了Z异构体7ab-db。这种发达的方法还为烯胺酮10a-c的合成提供了一种简便而新颖的途径。详细的工作还通过在铜催化的吲哚和吡咯并[2,1-a]异喹啉的铜催化串联合成中优先添加邻卤代芳基炔烃,然后进行分子内C2芳基化来支持顺式异构体的形成。

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