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Synthesis of Hydrazones
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Tosyl- and Boc-hydrazones were found to be effective nucleophiles in the
Mitsunobu reaction. Tosyl hydrazones reacted cleanly with primary and
secondary alcohols when co-administered to a cooled DBAD/PPh3 or
DEAD/PPh3 complex.
J. M. Keith, L. Gomez, J. Org. Chem., 2006,
71, 7113-7116.
Central to an alternative source of substrates for Fischer indolizations was a
palladium-catalyzed coupling to prepare N-aryl benzophenone hydrazones.
Hydrolysis of the hydrazones in the presence of ketones produced enolizable
hydrazones that underwent Fischer indolization.
S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc., 1998,
120, 6621-6622.
(R)-DTBM-Segphos-Pd(0) catalyzes a hydrohydrazonation of
1,4-disubstituted 1,3-dienes to provide allylic chiral hydrazones in good yields
with good regio- and enantioselectivity. This transformation tolerates a wide
range of substrates and functional groups.
S. Sun, Q. Zhang, W. Zi, Org. Lett., 2023, 25,
8397-8401.
A metal-free photocatalytic coupling reaction of
α-diazoacetates and alkyl N-hydroxyphthalimide esters provides structurally and functionally diverse
N-alkyl hydrazones. By employing Rose Bengal
as a photocatalyst with yellow LEDs irradiation and Hantzsch ester as both an electron donor and
proton source, over 60 N-alkyl hydrazones were
synthesized.
C.-M. Chan, Q. Xing, Y.-C. Chow, S.-F. Hung, W.-Y. Yu,
Org. Lett., 2019, 21, 8037-8043.
A general two-step synthesis of substituted 3-aminoindazoles from
2-bromobenzonitriles involves a palladium-catalyzed arylation of benzophenone
hydrazone followed by an acidic deprotection/cyclization sequence. This
procedure offers a general and efficient alternative to the typical SNAr
reaction of hydrazine with o-fluorobenzonitriles.
V. Lefebvre, T. Cailly, F. Fabis, S. Rault, J. Org. Chem., 2010,
75, 2730-2732.
A highly chemo- and regioselective allylic amination of various hydrazones and hydrazides with allylic
carbonates proceeds at ambient temperature in the presence of an [Ir(COD)Cl]2/pyridine
catalyst, ammonium iodide, and diethylzinc to afford the corresponding N-allylation products in high yields.
R. Matunas, A. J. Lai, C. Lee, Tetrahedron, 2005,
61, 6298-9308.