Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(21), P. 3481 - 3484
Published: Jan. 1, 2022
A
method
to
functionalize
the
arene
ring
of
pirfenidone
has
been
demonstrated
using
pyridone
as
a
directing
group.
Unlike
functionalization
nucleus,
here
is
alkenylation
N-aryl
with
internal
alkynes
ruthenium
catalyst.
High
functional
group
tolerance,
simple
reaction
conditions
and
site-selective
permit
synthesis
new
analogues
drugs
in
step-economical
manner.
The
data
control
experiments
suggest
possibilities
base-assisted
electrophilic
substitution
(BIES)
pathway.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(4), P. 786 - 791
Published: Jan. 22, 2024
Presented
herein
is
an
unprecedented
synthesis
of
naphtho[1′,2′:4,5]furo[3,2-b]pyridinones
via
Ir(III)-catalyzed
C6/C5
dual
C–H
functionalization
N-pyridyl-2-pyridones
with
diazonaphthalen-2(1H)-ones.
This
protocol
forms
C–C
and
C–O
bonds
in
one
pot
which
diazonaphthalen-2(1H)-ones
serve
as
bifunctional
reagents,
providing
both
alkyl
aryloxy
sources.
To
the
best
our
knowledge,
this
first
example
title
compounds
by
using
substrates.
Notably,
method
features
operational
simplicity,
good
functional
group
tolerance,
high
efficiency,
atom
economy.
ACS Catalysis,
Journal Year:
2021,
Volume and Issue:
11(8), P. 4606 - 4612
Published: April 1, 2021
Conventional
C–H
alkenylation
with
alkynes
via
low-valent
transition-metal
catalysis
occurs
at
the
C6
or
C4
position
of
2-pyridone
electron-deficient
bonds.
A
bifunctional
ligand-bonded
Ni–Al
bimetallic
catalyst
resulted
in
a
reversed
selectivity,
providing
series
C3-alkenylated
2-pyridones
up
to
99%
yields.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(14), P. 5277 - 5283
Published: Jan. 1, 2024
Chemodivergent
construction
of
structurally
distinct
heterocycles
from
the
same
precursors
by
adjusting
specific
reaction
parameters
is
an
emergent
area
organic
synthesis;
yet,
understanding
processes
that
underpin
divergence
lacking,
preventing
development
new
synthetic
methods
systematically
harnessing
key
mechanistic
effects.
We
describe
herein
cesium
carbonate-promoted
oxadiaza
excision
cross-coupling
reactions
β-ketoesters
with
1,2,3-triazine
1-oxides
form
pyridones
in
good
to
high
yields,
instead
sole
formation
pyridines
when
performed
presence
other
alkali
metal
carbonates
or
bases.
The
can
be
further
extended
synthetically
challenging
pyridylpyridones.
A
computational
study
comparing
effect
and
sodium
ions
reveals
cesium-coordinated
species
changes
preference
attack
at
ketone
carbonyl
ester
carbon
due
ion-specific
transition
state
conformational
accommodation,
revealing
a
previously
unexplored
role
may
facilitate
chemodivergent
approaches
heterocyclic
systems.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(43), P. 5626 - 5629
Published: Jan. 1, 2024
Isoquinolones
undergo
efficient
Co(
iii
)-catalyzed
C8-allylation
and
vinylation,
utilizing
the
oxo
group
of
isoquinolones
as
an
inherent
directing
group.
The
resulting
allylated
vinylated
are
further
transformed
into
important
building
blocks.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 3048 - 3053
Published: April 5, 2024
We
demonstrate
a
ligand-
and
glovebox-free
regioselective
direct
C(3)–H
imidation
of
2-pyridones
also
benzylic-type
bearing
methyl
substituent
employing
Cu(OAc)2·H2O
as
the
catalyst
N-fluorobenzenesulfonimide
(NFSI)
an
imidating
reagent.
A
broad
range
imidated
2-pyridone
derivatives
is
made
up
to
excellent
yields.
The
present
strategy
operates
well
on
gram
scale,
ensuing
product
can
be
readily
subjected
mono-
bis-desulfonylation
reactions.
Organic & Biomolecular Chemistry,
Journal Year:
2020,
Volume and Issue:
19(2), P. 394 - 398
Published: Dec. 8, 2020
A
visible-light-promoted
O-H
insertion
reaction
between
2-pyridones
and
α-aryldiazoacetates
has
been
developed.
Upon
visible
light
irradiation,
the
proceeds
smoothly
under
mild
catalyst-free
conditions.
wide
scope
of
are
well
tolerated,
various
O-alkylated
obtained
with
perfect
selectivity
good
functional
group
tolerance.
photoinduced
radical
process
is
probably
responsible
for
excellent
selectivity.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 8, 2025
A
remarkably
simple
and
efficient
double
defluorinative
[3
+
3]
annulation
approach
involving
N-phenyl-α-fluoro-α-phenylsulfonylacetamide
2-CF3-alkenes
to
access
N-phenyl-3,6-difluoropyridone
derivatives
has
been
achieved.
The
key
the
success
of
this
single-step
synthesis
difluoropyridones
is
strategic
utilization
for
consecutive
allylic
vinylic
substitution
reactions
a
desulfonylation
cascade.
We
could
also
show
that
these
serve
as
versatile
platform
C-6-selective
functionalizations.
