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3-Alkoxylmethyl-5-alkylpyrazoles undergo regioselective N-arylation with 4-fluoronitrobenzene in the presence of base to yield the corresponding 1-(4-nitro-phenyl)pyrazoles. Further elaboration of these intermediates furnishes a practical synthesis of unsymmetrical 3,5-dialkyl-1-arypyrazoles. A tentative explanation of the observed regioselectivities is provided.
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Wang et al. (2000) studied this question.
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