Categories: N-N Bond Formation >
Synthesis of Hydrazines (Hydrazides)
Related: |
Recent Literature
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.