Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
12(1)
Опубликована: Дек. 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.
Journal of Computational Chemistry,
Год журнала:
2022,
Номер
44(1), С. 27 - 42
Опубликована: Окт. 14, 2022
Algorithms
that
automatically
explore
the
chemical
space
have
been
limited
to
systems
with
a
low
number
of
atoms
due
expensive
involved
quantum
calculations
and
large
amount
possible
reaction
pathways.
The
method
described
here
presents
novel
solution
problem
exploration
by
generating
networks
heuristics
based
on
theory.
First,
second
version
network
is
determined
through
molecular
graph
transformations
acting
upon
functional
groups
reacting.
Only
break
two
bonds
form
new
ones
are
considered,
leading
significant
performance
enhancement
compared
previously
presented
algorithm.
Second,
energy
barriers
for
this
estimated
growing
string
method,
which
can
also
identify
non-octet
species
missed
during
previous
step
further
define
network.
proposed
algorithm
has
successfully
applied
five
different
reactions,
in
all
cases
identifying
most
important
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(35), С. 7095 - 7099
Опубликована: Янв. 1, 2023
Here
we
report
a
strategy
for
the
facile
assembly
of
fused
3-trifluoromethyl-1,2,4-triazoles,
which
are
difficult
to
synthesize
using
traditional
strategies,
in
50-96%
yields
through
triethylamine-promoted
intermolecular
[3
+
2]
cycloaddition
pathway.
This
protocol
features
high
efficiency,
good
functional
group
tolerance,
mild
conditions,
and
easy
operation.
Furthermore,
gram-scale
reaction
product
derivatizations
were
carried
out
smoothly
illustrate
practicability
this
method.
Molecules,
Год журнала:
2022,
Номер
27(23), С. 8446 - 8446
Опубликована: Дек. 2, 2022
A
solvent-free
two-step
synthesis
of
polyfunctionalized
pyrazoles
under
ball-milling
mechanochemical
conditions
was
developed.
The
protocol
comprises
(3
+
2)-cycloaddition
in
situ
generated
nitrile
imines
and
chalcones,
followed
by
oxidation
the
initially
formed
5-acylpyrazolines
with
activated
MnO2.
second
step
proceeds
via
an
exclusive
deacylative
pathway,
to
give
a
series
1,4-diarylpyrazoles
functionalized
fluorinated
(CF3)
or
non-fluorinated
(Ph,
COOEt,
Ac)
substituent
at
C(3)
heterocyclic
ring.
In
contrast,
MnO2-mediated
model
isomeric
4-acylpyrazoline
proceeded
low
chemoselectivity,
leading
fully
substituted
pyrazole
as
major
product
dehydrogenative
aromatization.
presented
approach
extends
scope
known
methods
carried
out
organic
solvents
enables
preparation
pyrazoles,
which
are
general
interest
medicine
material
sciences.
RSC Advances,
Год журнала:
2022,
Номер
12(21), С. 13087 - 13092
Опубликована: Янв. 1, 2022
A
highly
efficient
potassium
carbonate-mediated
[3
+
2]
cycloaddition
reaction
of
hydrazonoyl
chlorides
with
cinnamic
aldehydes
to
furnish
multi-substituted
pyrazoles
under
nontoxic
and
mild
conditions
has
been
developed.
plausible
stepwise
mechanism
is
proposed.
This
protocol
featured
broad
substrate
coverage,
good
functional
group
tolerance,
wide
scalability,
operational
simplicity,
as
well
conveniently
constructed
pyrazole
scaffolds.
Pharmaceutics,
Год журнала:
2023,
Номер
15(2), С. 498 - 498
Опубликована: Фев. 2, 2023
An
efficient,
eco-compatible,
and
very
cheap
method
for
the
construction
of
fully
substituted
pyrazoles
(Pzs)
via
eliminative
nitrilimine-alkene
1,3-dipolar
cycloaddition
(ENAC)
reaction
was
developed
in
excellent
yield
high
regioselectivity.
Enaminones
nitrilimines
generated
situ
were
selected
as
dipolarophiles
dipoles,
respectively.
A
deep
screening
employed
base,
solvent,
temperature
carried
out
to
optimize
conditions.
Recycling
tests
ionic
liquid
performed,
furnishing
efficient
performance
until
six
cycles.
Finally,
a
plausible
mechanism
proposed.
Then,
effect
three
different
structures
Pzs
evaluated
on
F1FO-ATPase
activity
mitochondrial
permeability
transition
pore
(mPTP)
opening.
The
Pz
derivatives’
titration
curves
6a,
6h,
6o
showed
reduced
86%,
35%,
31%,
Enzyme
inhibition
analysis
depicted
an
uncompetitive
with
typical
formation
tertiary
complex
enzyme-substrate-inhibitor
(ESI).
dissociation
constant
ESI
(Ki’)
presence
6a
had
lower
order
magnitude
than
other
Pzs.
pyrazole
core
might
set
specific
F1FO-ATPase,
whereas
functional
groups
modulate
binding
affinity.
mPTP
opening
decreased
Pz-treated
mitochondria
Pzs’
inhibitory
concentration-dependent
6o.
Indeed,
more
efficiently
blocked
0.1
mM
1
6a.
On
contrary,
stronger
desensitization
is
target
blocking
formation.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(24), С. 16820 - 16828
Опубликована: Дек. 7, 2022
Here,
we
report
the
synthesis
of
3,4-disubstituted
1H-pyrazoles
and
3,5-disubstituted
pyridines
from
reaction
epoxides
with
hydrazine
ammonia,
respectively.
Both
reactions
utilize
Sc(OTf)3
as
a
Lewis
acid.
The
pyrazole
utilizes
N-bromosuccinimide
to
convert
intermediate
pyrazolines
pyrazoles,
whereas
pyridine
FeCl3
cocatalyst.
Beilstein Journal of Organic Chemistry,
Год журнала:
2023,
Номер
19, С. 1741 - 1754
Опубликована: Ноя. 15, 2023
Nitrogen-containing
organofluorine
derivatives,
which
are
prepared
using
fluorinated
building
blocks,
among
the
most
important
active
fragments
in
various
pharmaceutical
and
agrochemical
products.
This
review
focuses
on
reactivity,
synthesis,
applications
of
fluoromethylated
hydrazones
acylhydrazones.
It
summarizes
recent
methodologies
that
have
been
used
for
synthesis
nitrogen-containing
compounds.
