Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of Hydrazine Derivatives
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Recent Literature
An environmentally benign, tin-free radical "on water" addition of alkyl
iodides to the C=N bond of hydrazones in the presence of diphenylsilane and
triethylborane afforded the corresponding addition products in good yields.
The developed protocol can be applied to the synthesis of 3-substituted
isoindolinone derivatives.
T. K. Nam, D. O. Jang, J. Org. Chem., 2018, 83,
7373-7379.
Cu-catalyzed and metal-free conditions developed for allyltrimethoxysilane
addition to N-benzoylhydrazones enable efficient and versatile access to
homoallylic α-branched amines. Aldehyde hydrazones, both aromatic and aliphatic,
and ketone hydrazones all give good yields.
H. Ding, G. K. Friestadt, Synthesis,
2004, 2216-2221.
The reaction of allylboronic acids with acyl hydrazones proceeds with very high
syn selectivity to afford homoallylic amine derivatives. The reaction can be
carried out with both aromatic and aliphatic acyl hydrazones. The excellent syn
stereochemistry, which is the opposite of the stereochemistry observed for
allylboration of imines, can be explained by chelation control of the acyl
hydrazone and the B(OH)2 moiety.
A. Das, R. Alam, L. Eriksson, K. J. Szabo, Org. Lett., 2014,
16, 3808-3811.