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© Institut Pasteur
Cristaux de cellulase, enzyme purifiée de Clostridium thermocellum permettant la digestion de la cellulose. Image colorisée.
Publication : Chemistry (Weinheim an der Bergstrasse, Germany)

5-Iodo-3-ethoxypyrazoles: an entry point to new chemical entities

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Chemistry (Weinheim an der Bergstrasse, Germany) - 23 Mar 2010

Guillou S, Janin YL

Link to Pubmed [PMID] – 20333718

Chemistry 2010 Apr;16(15):4669-77

Our program, which has focused on the preparation of new pyrazole derivatives, has led us to report here an original and simplified preparation of ethyl 3-ethoxy-1H-pyrazole-4-carboxylate. This is based on the reaction of hydrazine monohydrochloride and diethyl 2-(ethoxymethylene)malonate. Further transformations of this key compound allowed the preparation of the two possible iodinated isomers, namely, 3-ethoxy-4-iodo- and 3-ethoxy-5-iodo-1H-pyrazole. These compounds have opened the way to a quick access to many original pyrazole series. As an illustration, we report here on the selectivity of N-arylation, by using the Lam and Cham method, the C4- and C5-arylation of some of these 3-ethoxypyrazole derivatives by using the Suzuki-Miyaura reaction, and C5-benzylation reactions by means of the Negishi reaction. This was followed by hydrolysis of the ethoxy group, which led to the corresponding pyrazol-3-one derivatives. As a conclusion of this work, we conducted an investigation into the regiochemistry of the condensation between diethyl 2-(ethoxymethylene)malonate and the hydrochloride salts of methyl, benzyl, or phenyl hydrazine.

http://www.ncbi.nlm.nih.gov/pubmed/20333718