Add time:07/13/2019         Source:sciencedirect.com

2-(Furan-2-yl)- and 2-(thiophen-2-yl)pyrroles are readily ethynylated with acylbromoacetylenes in the solid Al2O3 medium (no solvent, room temperature, 1 h) to afford 5-(furan-2-yl)- and 5-(thiophen-2-yl)-2-acylethynylpyrroles in 39–74% yields. In the case of 2-(furan-2-yl)pyrroles, an alternative ethynylation of the furan ring takes place, the ratio of the furan and pyrrole ring ethynylation products being 1:5–7. No ethynylation of the thiophene ring as well as ethynylation of both heterocycles in a one molecule has been detected. Thus the reactivity of the heterocycles towards the ethynylation system (acylbromoacetylenes/Al2O3) falls in the order: pyrrole>furan>thiophene.

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