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Formation of Complex Hydrazine Derivatives via Aza-Lossen Rearrangement

Dilan E. Polat, David D. Brzezinski, André M. Beauchemin*

*Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada, Email: andre.beaucheminuottawa.ca

D. E. Polat, D. D. Brzezinski, A. M. Beauchemin, Org. Lett., 2019, 21, 4849-4852.

DOI: 10.1021/acs.orglett.9b01742


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Abstract

A broadly applicable procedure for an aza-Lossen rearrangement converts amines into complex hydrazine derivatives in two steps under safe, mild conditions. This method allows the chemoselective formation of N-N bonds, resulting in the synthesis of cyclic and acyclic products while avoiding side reactions of the amphoteric (ambident) nitrogen-substituted isocyanate intermediate.

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proposed reaction pathway



Key Words

hydrazines, urea derivatives


ID: J54-Y2019