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.
RSC Advances,
Journal Year:
2024,
Volume and Issue:
14(9), P. 5817 - 5845
Published: Jan. 1, 2024
A
variety
of
bioactive
compounds
can
be
synthesized
via
C–C
and
C–X
(X
=
O/S/N/Se/Cl/Br)
bond
formation
using
an
efficient
catalytic
system
I
2
/DMSO.
This
review
highlights
the
progress
identifies
potential
paths
for
future
research
in
this
field.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(33), P. 4872 - 4890
Published: Jan. 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.
Organic Chemistry Frontiers,
Journal Year:
2021,
Volume and Issue:
8(18), P. 5040 - 5044
Published: Jan. 1, 2021
Herein,
a
facile
and
straightforward
route
to
synthesize
3-trifluoromethyl-1,2,4-triazoles
via
copper-mediated
[3
+
2]
cycloaddition
of
trifluoroacetimidoyl
chlorides
N
-isocyanoiminotriphenylphosphorane
(NIITP)
has
been
described.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(5), P. 1044 - 1049
Published: Jan. 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,
Journal Year:
2022,
Volume and Issue:
27(19), P. 6568 - 6568
Published: Oct. 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.
Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(87), P. 12224 - 12227
Published: Jan. 1, 2022
A
general
and
regioselective
synthesis
of
3-trifluoromethyl
1,2,4-triazoles
has
been
achieved
through
photocycloaddition
sydnone
with
trifluoroacetonitrile.
This
method
employed
trifluoroacetaldehyde
O-(aryl)oxime
as
the
CF3CN
precursor
tolerated
various
functional
groups
to
furnish
1,2,4-triazole
products
in
moderate
good
yields.
Mechanistic
experiments
revealed
an
energy
transfer
from
photocatalyst
4-CzIPN
substrates.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(9), P. 5882 - 5892
Published: April 12, 2022
A
tandem
addition/cyclization
reaction
between
trifluoromethyl
N-acylhydrazones
and
cyanamide
is
described,
which
provides
a
novel
efficient
process
for
the
synthesis
of
polysubstituted
3-trifluoromethyl-1,2,4-triazolines
their
derivatives.
The
method
has
advantages
mild
conditions,
broad
substrate
scope,
good
product
yields,
atom
economy.
Organic Chemistry Frontiers,
Journal Year:
2021,
Volume and Issue:
8(21), P. 6089 - 6094
Published: Jan. 1, 2021
A
new
palladium-catalyzed
three-component
carbonylative
procedure
for
the
construction
of
5-trifluoromethyl-1,2,4-triazoles
from
trifluoroacetimidohydrazides
and
aryl
iodides
has
been
developed.
TFBen
is
applied
as
a
safe
convenient
solid
CO
surrogate
here.
Chinese Journal of Chemistry,
Journal Year:
2021,
Volume and Issue:
39(12), P. 3443 - 3447
Published: Sept. 29, 2021
Main
observation
and
conclusion
A
metal‐free
approach
for
the
synthesis
of
3‐hetaryl‐5‐trifluoromethyl‐1,2,4‐triazoles
via
sulfur/dimethyl
sulfoxide‐promoted
oxidative
cyclization
readily
available
trifluoroacetimidohydrazides
with
methylhetarenes
has
been
developed.
This
transformation
proceeds
in
cascade
sulfur‐mediated
generation
thioaldehyde,
condensation,
intramolecular
aromatization
sequence.
