Efficient Procedure for High-Yield Synthesis of 4-Substituted 3,5-Dinitropyrazoles Using 4-Chloro-3,5-dinitropyrazole

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 substitut...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2012-07, Vol.44 (13), p.2058-2064
Main Authors: Dalinger, Igor L., Vatsadze, Irina A., Shkineva, Tatyana K., Popova, Galina P., Shevelev, Svyatoslav A.
Format: Article
Language:English
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0031-1291134