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Synthesis of Hydrazines (Hydrazides)

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The electrophilic amination of primary aliphatic and aromatic amines with a diethylketomalonate-derived oxaziridine affords the corresponding N-Boc hydrazines in good to excellent yields. The method allows a one-pot synthesis of pyrazoles from primary amines.
A. Armstrong, L. H. Jones, J. D. Knight, R. D. Kelsey, Org. Lett., 2005, 7, 713-716.


A small ring phosphacycle (phosphetane) catalyzes the synthesis of unsymmetrical hydrazines by cross-selective intermolecular NN reductive coupling of nitroarenes and anilines in the presence of a hydrosilane as the terminal reductant. The reaction offers good chemoselectivity and functional group tolerance.
G. Li, S. P. Miller, A. T. Radosevich, J. Am. Chem. Soc., 2021, 143, 14464-14469.


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