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Copper(I) halide-promoted formation of 3-acyl-5-halopyridine moiety from NH-2-(2-acylethynyl)pyrroles and propargylamine

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Available NH-2-acylethynylpyrroles undergo annulation/aromatization with propargylamine in the presence of 1 equiv. of CuHal (Hal = Cl, Br, I) at 60–65 °C to afford 3-acyl-2-(pyrrol-2-yl)pyridines and their 5-halo analogues in 28–61 and 5–14%… Click to show full abstract

Available NH-2-acylethynylpyrroles undergo annulation/aromatization with propargylamine in the presence of 1 equiv. of CuHal (Hal = Cl, Br, I) at 60–65 °C to afford 3-acyl-2-(pyrrol-2-yl)pyridines and their 5-halo analogues in 28–61 and 5–14% yields, respectively. The latter are assumed to be resulted from halohydrogenation of the intermediate Cu-pyrrolylpropargyl amino enones.

Keywords: formation acyl; promoted formation; halide promoted; copper halide; halopyridine moiety; acyl halopyridine

Journal Title: Mendeleev Communications
Year Published: 2019

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