Frontiers in Chemistry,
Journal Year:
2022,
Volume and Issue:
10
Published: Sept. 20, 2022
A
convenient
approach
for
the
construction
of
pharmaceutically
valuable
3-trifluoromethyl-1,2,4-triazoles
has
been
developed,
which
employs
readily
available
trifluoroacetimidoyl
chlorides,
hydrazine
hydrate
and
benzene-1,3,5-triyl
triformate
(TFBen)
as
starting
materials.
The
multi-component
reaction
features
broad
substrate
scope,
high
efficiency,
scalability,
providing
a
facile
straightforward
route
to
biologically
important
3-trifluoromethyl-1,2,4-triazole
scaffolds
in
moderate
good
yields.
Considering
its
broad-spectrum
pharmaceutical
activity,
method
offers
opportunity
further
study
towards
toxicity
risk
assessment
structure-activity
relationship
pharmaceuticals
containing
trifluoromethyl-1,2,4-triazole
cores.
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(21), P. 4982 - 4987
Published: Oct. 2, 2021
Abstract
A
metal‐free
oxidative
cyclization
of
readily
available
trifluoroacetimidohydrazides
with
D‐glucose
for
the
assembly
3‐trifluoromethyl‐1,2,4‐triazoles
has
been
disclosed.
is
applied
as
C1
synthon
to
provide
methine
source
in
reaction.
Control
experiments
have
conducted
shed
light
on
reaction
mechanism.
The
synthetic
utility
protocol
explored
by
implementation
scale
up
and
synthesis
key
skeleton
NK
I
‐receptor
ligand.
magnified
image
Green Synthesis and Catalysis,
Journal Year:
2022,
Volume and Issue:
3(4), P. 385 - 388
Published: June 25, 2022
A
metal-free
approach
for
the
synthesis
of
3-trifluoromethyl-1,2,4-triazoles
via
I2-mediated
oxidative
cyclization
readily
accessible
trifluoroacetimidohydrazides
with
N,N-dimethylformamide
(DMF)
has
been
disclosed.
In
this
transformation,
commonly
used
organic
solvent
DMF
is
applied
as
a
C1
synthon
and
methine
unit
1,2,4-triazole
products
independently
from
N-methyl
N-acyl
DMF.
The
application
potential
developed
method
demonstrated
by
key
skeleton
factor
IXa
inhibitors.
Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
12(1)
Published: Dec. 15, 2022
Abstract
An
efficient
synthesis
of
densely
1,2,4‐triazoles
has
been
achieved
by
[3+2]
cycloaddition
nitrileimides
with
amidine
hydrochlorides
under
transition
metal‐free
conditions.
This
method
features
mild
reaction
conditions,
wide
substrate
scope
and
good
functional
group
tolerance.
A
series
aryl,
heterocyclic
alkyl
substituted
3‐CF
3
‐1,2,4‐triazoles
were
synthesized
smoothly
the
promotion
NaHCO
yield
up
to
96%.
In
addition,
both
gram‐scale
synthetic
transformations
are
elaborated
indicate
utility
this
reaction.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(8), P. 5277 - 5286
Published: April 8, 2024
A
general
and
practical
method
for
the
construction
of
various
3,4,5-trisubstituted
1,2,4-triazoles
via
I2-catalyzed
cycloaddition
N-functionalized
amidines
with
hydrazones
is
reported.
This
strategy
features
cheap
readily
available
catalyst
starting
materials,
broader
substrate
scope,
moderate-to-good
yields.
The
mechanism
study
shows
that
existence
hydrogen
on
nitrogen
crucial
this
transformation.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(30), P. 6380 - 6384
Published: July 22, 2024
A
novel
[1+1+3]
annulation
of
AgNOx,
isocyanides,
and
isocyanates
for
the
selective
synthesis
1,2,4-triazoles
is
presented
herein.
In
this
transformation,
AgNOx
are
used
as
nitrogen
sources
instead
traditional
hydrazine
or
diazonium
reagents.
This
process
also
involves
N-O/C-H/C═N
bond
cleavage
construction
new
N-N/C-N
bonds
with
a
good
substrate
scope
functional
group
tolerance.
Synthesis,
Journal Year:
2022,
Volume and Issue:
55(04), P. 683 - 691
Published: Aug. 30, 2022
Abstract
A
novel,
efficient,
and
solvent-free
approach
for
the
synthesis
of
aryl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles
is
disclosed
via
nucleophilic
intramolecular
cyclization
reaction
trifluoromethylated
amidrazone
2,2,2-trifluoroacetic
anhydride.
The
intermediates
used
in
this
project
are
synthesized
from
N-aryl-2,2,2-trifluoroacetimidoyl
chloride
derivatives
hydrazine
hydrate
at
ambient
temperature
excellent
yields.
Green Synthesis and Catalysis,
Journal Year:
2022,
Volume and Issue:
4(2), P. 177 - 180
Published: Aug. 17, 2022
A
simple
metal
and
additive-free
approach
for
the
assembly
of
5-trifluoromethyl-1,2,4-triazoles
via
only
heating-induced
decarboxylative
cyclization
readily
available
trifluoroacetimidohydrazides
α-oxocarboxylic
acids
has
been
developed.
In
this
protocol,
rarely
reported
tetrahedral
carboxylic
intermediate
could
be
in-situ
generated
undergo
subsequent
decarboxylation
to
afford
target
heterocycle
products.
Journal of Heterocyclic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 25, 2024
ABSTRACT
A
novel
series
of
N‐carbamimidoyl‐2,2,2‐trifluoro‐N′‐arylacetimidamides
(3a–j)
have
been
prepared
via
condensation
2,2,2‐trifuoroacetimidoyl
chlorides
with
guanidine
in
the
presence
Na
and
dry
EtOH
solvent
at
ambient
temperature.
Then,
these
key
intermediates
were
applied
for
synthesized
3‐amino‐4‐aryl‐5‐(trifluoromethyl)‐1H‐1,2,4‐triazoles
(4a–j)
under
oxidative
cyclization
reaction
KI/I
2
as
an
oxidant
system
DMSO
solvent.
The
target
compounds
produced
high
yields
without
need
isolation.
