原创力文档consecutive three-component synthesis of 3-(hetero)aryl-1h-pyrazoles with propynal diethylacetal as a three-carbon building block连续三分量合成3 -(异性恋)aryl-1h-pyrazoles propynal diethylacetal 3个碳构建块.pdfVIP
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consecutive three-component synthesis of 3-(hetero)aryl-1h-pyrazoles with propynal diethylacetal as a three-carbon building block连续三分量合成3 -(异性恋)aryl-1h-pyrazoles propynal diethylacetal 3个碳构建块
Molecules 2011, 16, 9340-9356; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Communication
Consecutive Three-Component Synthesis of
3-(Hetero)Aryl-1H-pyrazoles with Propynal
Diethylacetal as a Three-Carbon Building Block
Lucilla Levi, Christina Boersch, Charlotte F. Gers, Eugen Merkul and Thomas J. J. Müller *
Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf,
Universitätsstraße 1, D-40225 Düsseldorf, Germany
* Author to whom correspondence should be addressed; E-Mail: ThomasJJ.Mueller@uni-duesseldorf.de;
Tel.: +49-(0)211-8112298; Fax: +49-(0)211-8114324.
Received: 30 September 2011; in revised form: 19 October 2011 / Accepted: 21 October 2011 /
Published: 7 November 2011
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.
Keywords: alkyne; cyclocondensation; multi-component reaction; pyrazole; Sonogashira
coupling
1. Introduction
Pyrazoles, i.e., diazoles with two adjacent nitrogen atoms, display a rich chemistry and are used in
numerous applications [1-3]. Their broad spectrum of biological activities, such as anti-hyperglycemic,
analgesic, anti-inflammatory, antipyretic, anti-bacterial, and sedative-hypnotic properties, has attracted
considerable interest
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