Angewandte Chemie,
Год журнала:
2023,
Номер
136(8)
Опубликована: Ноя. 21, 2023
Abstract
An
arylation
protocol
for
pyridines
is
described,
via
the
ring‐opened
Zincke
intermediate.
Treatment
of
with
triflic
anhydride
and
a
secondary
amine
produces
an
azahexatriene
species,
which
undergoes
regioselective
Pd‐catalyzed
at
putative
C4
position.
Recyclization
then
provides
pyridine
products.
Alternatively,
metal‐free
diaryliodonium
salt
selective
meta
‐position,
affording
regiodivergent
approach
to
biaryls
from
common
Journal of the American Chemical Society,
Год журнала:
2023,
Номер
145(28), С. 15581 - 15588
Опубликована: Июль 10, 2023
para-Selective
C-H
functionalization
of
pyridines
holds
a
significant
value
but
remains
underdeveloped.
Site-switchable
under
easily
tunable
conditions
expedites
drug
development.
We
recently
reported
redox-neutral
dearomatization-rearomatization
strategy
for
meta-C-H
via
oxazino
pyridine
intermediates.
Here,
we
demonstrate
that
these
intermediates
undergo
highly
para-selective
simply
by
switching
to
acidic
conditions.
A
broad
scope
para-alkylated
and
arylated
is
prepared
through
radical
as
well
ionic
pathways.
These
mild
catalyst-free
methods
are
applied
the
late-stage
para-functionalization
drugs
using
limiting
reagents.
Consecutive
meta,para-difunctionalization
also
achieved
with
complete
regiocontrol
relying
on
pH-dependent
reactivity
pyridines.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(34)
Опубликована: Июль 3, 2023
Abstract
Herein,
we
report
a
one‐pot
method
for
enantioselective
C−H
allylation
of
pyridines
at
C3
via
tandem
borane
and
palladium
catalysis.
This
involves
borane‐catalyzed
pyridine
hydroboration
to
generate
dihydropyridines,
then
palladium‐catalyzed
the
dihydropyridines
with
allylic
esters,
finally
air
oxidation
allylated
afford
products.
enables
introduction
an
group
excellent
regio‐
enantioselectivities.
Saudi Pharmaceutical Journal,
Год журнала:
2024,
Номер
32(5), С. 102025 - 102025
Опубликована: Март 12, 2024
Based
on
previous
developments
of
our
research
programs
in
trying
to
find
new
compounds
with
multiple
biological
targets
such
as
antioxidant,
anti-diabetic,
anti-Alzheimer's,
and
anti-arthritic
agents.
In
the
context,
a
novel
series
sulfonamide
derivatives
based
pyrazole
or
pyridine
moieties
3a,
b,
7–9,
11–13,
15a,
16
were
synthesized
from
amine
sulfonyl
chloride
derivatives.
The
structures
elucidated
via
spectroscopy
(1H
13C
NMR).
biologically
assessed
vitro
for
their
anti-diabetic
(α-amylase
α-glucosidase
inhibition)
anti-Alzheimer's
(acetylcholinesterase
activities.
results
revealed
that
compound
15a
is
powerful
enzyme
inhibitor
α-amylase
α-glucosidase.
Also,
15b
demonstrated
activity
against
acetylcholinesterase
enzyme.
structure–activity
relationship
study
was
accomplished.
Furthermore,
complementary
silico
molecular
properties,
drug-likeness,
ADMET
prediction,
surface
properties
two
more
fulfilled
computed.
These
studies
recommend
candidates
modifications
before
vivo
assays.
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Май 15, 2024
Abstract
Difluoromethyl
pyridines
have
gained
significant
attention
in
medicinal
and
agricultural
chemistry.
The
direct
C−H-difluoromethylation
of
represents
a
highly
efficient
economic
way
to
access
these
azines.
However,
the
meta-difluoromethylation
has
remained
elusive
methods
for
site-switchable
regioselective
meta-
para-difluoromethylation
are
unknown.
Here,
we
demonstrate
meta-C−H-difluoromethylation
through
radical
process
by
using
oxazino
pyridine
intermediates,
which
easily
accessed
from
pyridines.
selectivity
can
be
readily
switched
para
situ
transformation
pyridinium
salts
upon
acid
treatment.
preparation
various
para-difluoromethylated
this
approach
is
presented.
mild
conditions
used
also
allow
late-stage
or
containing
drugs.
Sequential
double
functionalization
presented,
further
underlines
value
work.
Journal of the American Chemical Society,
Год журнала:
2025,
Номер
147(9), С. 7485 - 7495
Опубликована: Фев. 24, 2025
meta-Nitration
of
azines
(pyridines
and
quinolines)
serves
as
a
powerful
method
for
the
prompt
construction
derivatization
several
pharmaceuticals,
agrochemicals,
materials.
However,
due
to
inherent
electronic
properties
pyridines,
achieving
direct
selective
meta-C-H
nitration
under
mild
conditions
has
been
long-standing
challenge
in
synthetic
chemistry.
Currently,
there
is
no
adequate
strategy
late-stage
pyridine-containing
drugs
drug
precursors.
To
address
this
void,
we
introduce
practical
protocol
highly
regioselective
meta-nitration
pyridines
using
dearomatization-rearomatization
strategy.
The
introduced
provides
diversification
platform
at
meta-position
via
radical
pathway.
This
mild,
open-air,
one-pot,
scalable,
catalyst-free
process
employed
pyridine
containing
drugs,
precursors,
ligands
limiting
reagents.
Consecutive
C3
C5
difunctionalization
also
achieved
with
complete
regiocontrol
relying
on
sequential
addition,
which
further
highlights
potential
presented
work.
Additionally,
obtained
products
could
be
transformed
into
meta-amino
azine
other
valuable
building
blocks.
Incorporating
N-heterocyclic
amine
structures
through
amidation
ibuprofen
significantly
improved
drug's
clinical
success,
highlighting
importance
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(35), С. 24257 - 24264
Опубликована: Авг. 22, 2024
The
C–H
hydroxylation
of
the
pyridine
C3
position
is
a
highly
desirable
transformation
but
remains
great
challenge
due
to
inherent
electronic
properties
this
heterocycle
core
which
bring
difficulties
in
chemical
reactivity
and
regioselectivity.
Herein
we
present
an
efficient
method
for
formal
selective
pyridines
via
photochemical
valence
isomerization
N-oxides.
This
metal-free
features
operational
simplicity
compatibility
with
diverse
array
functional
groups,
resulting
hydroxylated
products
are
amenable
further
elaboration
synthetically
useful
building
blocks.
synthetic
utility
strategy
demonstrated
effective
late-stage
functionalization
pyridine-containing
medicinally
relevant
molecules
versatile
derivatizations
3-pyridinols.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(45), С. 30758 - 30763
Опубликована: Ноя. 1, 2024
Organofluorine
compounds,
including
fluorinated
pyridines
and
isoquinolines,
play
a
crucial
role
in
pharmaceuticals,
agrochemicals,
materials
science.
However,
step-economic
selective
C-H-functionalization
to
access
these
azaarenes
is
still
underexplored,
with
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
63(8)
Опубликована: Ноя. 21, 2023
Abstract
An
arylation
protocol
for
pyridines
is
described,
via
the
ring‐opened
Zincke
intermediate.
Treatment
of
with
triflic
anhydride
and
a
secondary
amine
produces
an
azahexatriene
species,
which
undergoes
regioselective
Pd‐catalyzed
at
putative
C4
position.
Recyclization
then
provides
pyridine
products.
Alternatively,
metal‐free
diaryliodonium
salt
selective
meta
‐position,
affording
regiodivergent
approach
to
biaryls
from
common
