Categories: C=N Bond Formation >
Synthesis of hydrazones
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A catalytic acceptorless dehydrogenative coupling of arylhydrazines and
alcohols enables a direct synthesis of arylhydrazones with complete selectivity
for arylhydrazones without N-alkylated byproducts. This process provides a new
horizon for the development of catalytic acceptorless dehydrogenative coupling
reactions.
F. Li, C. Sun, N. Wang, J. Org. Chem., 2014,
79, 8031-8039.
N-tert-butyldimethylsilylhydrazone (TBSH) derivatives from
carbonyl-containing compounds serve as superior alternatives to simple
hydrazones in Wolff-Kishner-type reduction reactions, in the Barton vinyl
iodide preparation, in the synthesis of vinyl bromides, and in the synthesis
of gem-diiodides, gem-dibromides, and gem-dichlorides.
M. E. Furrow, A. G. Myers, J. Am. Chem. Soc.,
2004, 126, 5436-5445.
A variety of azides were treated with N,N-dimethylhydrazine in the
presence of ferric chloride hexahydrate as catalyst in refluxing acetonitrile to
provide pure hydrazones.
I. C. Barrett, J. D. Langille, M. A. Kerr, J. Org. Chem., 2000,
65, 6268-6269.
A Michael addition of amines and hydrazines to nitrostyrenes provides N-alkyl/aryl
substituted benzyl imines and N-methyl/phenyl substituted benzyl
hydrazones via a retro-aza-Henry-type process under mild, noncatalytic
conditions. The method can be used for the synthesis of biologically important
N-methyl pyrazoles in a one-pot manner, simple starting with the
corresponding nitrostyrenes and the methylhydrazine.
M. G. Kallitsakis, P. D. Tancini, M. Dixit, G. Mpourmpakis, I. N. Lykakis, J. Org. Chem.,
2018, 83, 1176-1184.
An electrooxidation of benzylic C(sp3)-H bonds to produce
hydrazones avoids the use of hazardous metal catalysts and external oxidants in
aqueous media in the presence of NaCl as cheap electrolyte. This strategy
provides hydrazones with various functional groups in good efficiency while the
highly oxidizable hydrazide group remains intact. The reaction is suitable for gram-scale synthesis.
I. Yavari, S. Shaabanzadeh, J. Org. Chem., 2022, 87,
15077-15085.
A facile gold-catalyzed hydrohydrazidation of alkynes with various hydrazides
provides a wide range of substituted keto-N-acylhydrazones in very good
yields under mild conditions. The reaction exhibits high functional group
tolerance, and is insensitive to electronic and steric effects.
D. P. Zimin, D. V. Dar'in, V. A. Rassadin, V. Y. Kukushkin, Org. Lett.,
2018, 20, 4880-4884.
Alkynyl hydrazones can be conveniently synthesized from 2-oxo-3-butynoates and
hydrazine without formation of pyrazoles. The resultant
hydrazones are transformed into alkynyl diazoacetates under mild oxidative conditions in excellent yields. Further,
alkynyl cyclopropane and
propargyl silane carboxylates are synthesized in good yields using copper-catalyzed alkynyl carbene transfer reactions.
A. Sharma, P. Jamwal, H. Vaid, R. Gurubrahamam, Org. Lett., 2023, 25,
1889-1894.
A mild diazenylation of active methylene compounds and N-heterocyclic
compounds with arylhydrazine hydrochlorides is mediated by iodine under basic
aerobic conditions. The reaction could be executed either under heating or in
the presence of blue LED light.
D. S. Barak, S. U. Dighe, I. Avasthi, S. Batra, J. Org. Chem., 2018, 83,
3361-3366.