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February 27, 2008Organic Letters135 citations

Base-Mediated Reaction of Hydrazones and Nitroolefins with a Reversed Regioselectivity:  A Novel Synthesis of 1,3,4-Trisubstituted Pyrazoles

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XDXiaohu DengNMNeelakandha S. Mani

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Abstract

A regioselective synthesis of 1,3,4-tri- or 1,3,4,5-tetrasubstituted pyrazoles by the reaction of hydrazones with nitroolefins is described. Mediated with strong bases such as t-BuOK, the reaction exhibits a reversed, exclusive 1,3,4-regioselectivity. Subsequent quenching with strong acids such as TFA is essential to achieve good yields. A plausible stepwise cycloaddition reaction mechanism is proposed.

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Cite This Study

Deng et al. (2008) studied this question.

synapsesocial.com/papers/6a5c7ea6bf1f0b83440027fchttps://doi.org/10.1021/ol800200j
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