Synthesis of 2,2-di(pyrazol-1-yl)enones via the 2:1 coupling of pyrazoles and acylbromoacetylenes in solid alumina

Add time:08/29/2019    Source:sciencedirect.com

Pyrazoles were reacted with acylbromoacetylenes in solid Al2O3 at room temperature to afford 2,2-di(pyrazol-1-yl)enones in 22–69% yield. The reaction proceeds via isolable intermediates, (Z)-2-bromo-2-(pyrazol-1-yl)enones. This unexpected 2:1 coupling is in contrast to similar reactions of pyrroles, furans and thiophenes, which give the corresponding acylethynyl derivatives. This reaction opens a one-pot route to inaccessible gem-dipyrazolylenones, which have potential applications as bidentate chelating ligands and building blocks for drug design.

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