Frontiers in Chemistry,
Год журнала:
2022,
Номер
10
Опубликована: Сен. 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.
Organic Letters,
Год журнала:
2022,
Номер
24(37), С. 6822 - 6827
Опубликована: Сен. 9, 2022
A
straightforward
strategy
for
the
metal-free
construction
of
trifluoromethyl-containing
pyrazole
derivatives
has
been
achieved
from
readily
available
α-halo
hydrazones
and
CF3-imidoyl
sulfoxonium
ylides.
The
cascade
transformation
proceeds
through
formal
[4+1]
cycloaddition
followed
by
an
unexpected
dual
double
bond
isomerization.
protocol
features
mild
conditions,
easy
operation,
excellent
substrate
compatibility,
good
regioselectivity.
synthetic
utility
is
demonstrated
scale-up
reaction
further
elaboration
obtained
products.
Chemical Communications,
Год журнала:
2023,
Номер
59(33), С. 4872 - 4890
Опубликована: Янв. 1, 2023
Recent
advances
in
the
direct
synthesis
of
trifluoromethyl-containing
heterocycles
from
trifluoroacetimidoyl
chlorides
(TFAICs)
and
derivatives,
including
trifluoroacetimidohydrazides
(TFAIHs)
CF3-imidoyl
sulfoxonium
ylides
(TFISYs),
are
systematically
summarized
discussed.
The
cascade
annulation
reactions
synthons
with
suitable
coupling
partners
have
emerged
as
a
powerful
promising
tool
for
construction
variety
trifluoromethyl-substituted
heterocycles.
Compared
other
building
blocks,
TFAICs
derivatives
notable
merits
easy
availability
handling,
relative
stability
safety,
high
reactivity.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(9), С. 1521 - 1525
Опубликована: Март 31, 2023
Abstract
An
approach
for
the
construction
of
5‐trifluoromethyl‐1,4‐dihydro‐1,2,4‐triazines
has
been
developed
via
base‐mediated
[3+3]
cycloaddition
in‐situ
generated
nitrile
imines
and
CF
3
‐substituted
imidoyl
sulfoxonium
ylides.
The
metal‐free
protocol
is
characterized
by
readily
available
starting
materials,
mild
conditions,
a
broad
substrate
scope,
high
efficiency,
good
synthetic
prospect,
scalability.
magnified
image
Chemical Communications,
Год журнала:
2022,
Номер
59(3), С. 318 - 321
Опубликована: Дек. 7, 2022
A
rhodium(III)-catalyzed
regioselective
C2-alkenylation
of
indoles
for
the
construction
α-CF3
substituted
enamines
has
been
developed,
which
utilizes
CF3-imidoyl
sulfoxonium
ylides
(TFISYs)
as
alkenylating
agents
first
time.
wide
array
indolyl-
and
trifluoromethyl-decorated
enamine
derivatives
have
assembled
in
moderate
to
good
yields.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(5), С. 1044 - 1049
Опубликована: Янв. 22, 2022
Abstract
A
copper‐catalyzed
intramolecular
decarbonylative
cyclization
reaction
of
isatins
and
trifluoroacetimidohydrazides
for
the
synthesis
2‐(5‐trifluoromethyl‐1,2,4‐triazol‐3‐yl)aniline
derivatives
has
been
developed.
This
transformation
proceeds
through
a
cascade
condensation,
hydrolysis,
decarboxylation,
C−N
bond
formation
sequence.
The
obtained
1,2,4‐triazole
products
bearing
free
amino
group
can
be
readily
converted
into
other
useful
compounds.
magnified
image
Molecules,
Год журнала:
2022,
Номер
27(19), С. 6568 - 6568
Опубликована: Окт. 4, 2022
We
herein
describe
a
general
approach
to
5-trifluoromethyl
1,2,4-triazoles
via
the
[3
+
2]-cycloaddition
of
nitrile
imines
generated
in
situ
from
hydrazonyl
chloride
with
CF3CN,
utilizing
2,2,2-trifluoroacetaldehyde
O-(aryl)oxime
as
precursor
trifluoroacetonitrile.
Various
functional
groups,
including
alkyl-substituted
chloride,
were
tolerated
during
cycloaddition.
Furthermore,
gram-scale
synthesis
and
common
downstream
transformations
proved
potential
synthetic
relevance
this
developed
methodology.
Green Synthesis and Catalysis,
Год журнала:
2022,
Номер
3(4), С. 385 - 388
Опубликована: Июнь 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.
Synthesis,
Год журнала:
2022,
Номер
55(04), С. 683 - 691
Опубликована: Авг. 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.
