Abstract
Reactions of 3-methyl-1,4-dinitro-1H-pyrazole with phenylhydrazine and some C-substituted derivatives were studied. The reactions with arylhydrazines containing electron-withdrawing substituents afforded 1-Aryl-5-methyl-4-nitro-1H-pyrazoles only. Unexpectedly, mixtures of two regioisomers, 1-Aryl-3-methyl-4-nitro-1H-pyrazoles and 1-Aryl-5-methyl-4-nitro-1H-pyrazoles, were obtained from the reaction with phenylhydrazine or 4-methyl-and 4-fluoro-derivatives. An ANRORC (Addition of the Nucleophile, Ring Opening, Ring Closure) mechanism was proposed for the reaction.
| Original language | English |
|---|---|
| Pages (from-to) | 63-76 |
| Number of pages | 14 |
| Journal | Arkivoc |
| Volume | 2015 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - 28 Aug 2015 |
Keywords
- 3-methyl-1
- 4-dinitro-1H-pyrazole
- ANRORC
- Arylhydrazines
- Arylnitropyrazole
ASJC Scopus subject areas
- Organic Chemistry
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