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Synthesis 2012; 44(13): 2058-2064
DOI: 10.1055/s-0031-1291134
DOI: 10.1055/s-0031-1291134
paper
Efficient Procedure for High-Yield Synthesis of 4-Substituted 3,5-Dinitropyrazoles Using 4-Chloro-3,5-dinitropyrazole
Further Information
Publication History
Received: 26 November 2011
Accepted after revision: 17 April 2012
Publication Date:
04 June 2012 (online)
Abstract
The transformations of readily available 4-chloro-3,5-dinitropyrazole and its N-methylated derivative under the action of anionic S-/O-nucleophiles and neutral N-nucleophiles were studied. Independent of the substrate’s charge (anionic, R = H, or neutral, R = Me), the nucleophilic substitution proceeds exclusively at position 4 replacing the chlorine nucleofuge. As a result of this study, the effective synthetic method for the preparation of 4-substituted 3,5-dinitropyrazoles via the nucleophilic substitution in 4-chloro-3,5-dinitropyrazole was elaborated.
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