American Chemical Society
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A Practical Approach to Semicarbazone and Hydrazone Derivatives via Imino-isocyanates

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posted on 2013-08-16, 00:00 authored by Keira Garland, Wei Gan, Charlotte Depatie-Sicard, André M. Beauchemin
Complex hydrazone derivatives can be accessed readily from hydrazones upon heating in the presence of nucleophiles. This reactivity likely involves imino-isocyanate intermediates, and a variety of leaving groups can be used at temperatures ranging from 20 to 150 °C. Alcohols, thiols, primary, and secondary amines can be used as nucleophiles, thus providing a simple alternative to the synthesis of hydrazones via condensation on the parent carbonyl precursor and allowing late-stage derivatization.