Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering , East China Normal University , 500 Dongchuan Road , Shanghai 200241 , China.
Org Lett. 2018 Jul 6;20(13):3907-3910. doi: 10.1021/acs.orglett.8b01492. Epub 2018 Jun 20.
A transition-metal-free tandem process for the synthesis of substituted quinolin-4(1 H)-ones or enaminones is presented. A base-promoted insertion of ynones into the C-N σ-bond of amides is the key step in this process, which provides the corresponding aminoacylation products in good to high yields. Quinolin-4(1 H)-ones are selectively formed via the subsequent N-cyclization pathway in the cases of ynones bearing an ortho-bromo-substituted aryl ring. Easily accessible starting materials and high atom economy make this procedure attractive.
本文报道了一种用于合成取代的喹啉-4(1H)-酮或烯胺酮的无过渡金属串联反应。该过程的关键步骤是在酰胺的 C-N σ 键中，通过炔酮的碱促进插入反应，以良好至高的收率得到相应的氨酰化产物。对于带有邻位溴取代芳基环的炔酮，通过后续的 N-环化途径可选择性地生成喹啉-4(1H)-酮。该方法具有原料易得、原子经济性高等优点。
