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A simple method for the regiocontrolled synthesis of the 4,5‐disubstituted N‐phenylpyrazole regioisomers 2 and 3 from β‐enamino diketones and phenylhydrazine is described. Pyrazole 2 was prepared regioselectively by carrying out the reaction in a protic solvent, whereas pyrazole 3 was obtained as the main product by using an aprotic solvent. Steric factors regarding the β‐enamino diketones also influenced the regiochemistry of 2 and 3. The influence of solvent on the reaction outcome can be rationalized by using Fukui indices. The structures of 2 and 3 were unambiguously elucidated by 1H and 13C NMR spectroscopy, two‐dimensional HMBC experiments, high resolution mass spectrometry, and X‐ray crystallographic analysis.
Asian Journal of Organic Chemistry – Wiley
Published: May 1, 2017
Keywords: ; ; ; ;
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