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Consecutive Three-Component Synthesis of 3-(Hetero)Aryl-1H-pyrazoles with Propynal Diethylacetal as a Three-Carbon Building Block

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Author(s): Lucilla Levi | Christina Boersch | Charlotte F. Gers | Eugen Merkul | Thomas J. J. Müller

Journal: Molecules
ISSN 1420-3049

Volume: 16;
Issue: 11;
Start page: 9340;
Date: 2011;
Original page

Keywords: alkyne | cyclocondensation | multi-component reaction | pyrazole | Sonogashira coupling

ABSTRACT
A novel consecutive three-component synthesis of 3-(hetero)aryl-1H-pyrazoles via room temperature Sonogashira arylation of propynal diethylacetal used as a propargyl aldehyde synthetic equivalent has been disclosed. The final acetal cleavage-cyclocondensation with hydrazine hydrochloride at 80 °C rapidly furnishes the title compounds in a one-pot fashion.

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