CuBr_2/O_2促进N-芳基-β-烯胺酯分子内氧化环合反应构建2,3-二取代吲哚

CuBr_2/O_2 promoted the intramolecular oxidative cyclization of N-aryl-β-enamino esters for the construction of 2,3-disubstitued indoles

吲哚类化合物作为一类具有广泛生物和药理活性的有机分子,其合成研究具有重要的价值。而通过N-芳基烯胺的分子内氧化偶联反应构建吲哚类化合物成为合成吲哚类化合物最直接、高效的方法之一,得到合成化学家的广泛关注。基于此,本文发展以便宜的二价铜盐(CuBr_2)、绿色氧化剂(O_2)和吡啶作为配体共同促进的N-芳基-β-烯胺酯的分子内氧化环合反应,以58%~94%的收率成功地合成一系列2,3-二取代的吲哚类化合物,并对其进行核磁共振氢谱和碳谱表征。该合成策略为吲哚类化合物的合成提供了新的方法。

As a kind of organic molecules with wide biological and pharmacological activities, indoles are of great value in synthetic study. The directed intramolecular oxidative coupling of N-aryl enamine has become one of the most direct and efficient methods for the synthesis of indole-based compounds, and have attracted much attention from synthetic chemists. Thus in this paper, the intramolecular oxidative cyclization of N-aryl-β-enamino esters with the cheap copper （ II ） salt CuBrz, green oxidant O2 and pyridine as the ligand was developed, and a series of different 2,3-disubstituted indole compounds were successfully synthesized with 58%-94% yield, and the products were characterized by 1H NMR and 13C NMR. The strategy provides a new method for the synthesis ofindole compounds.