The
diazo
quinone
or
diazide
compounds
have
been
extensively
utilized
to
introduce
phenol/naphthol
moieties
into
hydrocarbons
nitrogen-containing
heterocycles
under
transition
metal
catalysis
[1].
reactions
proceed
via
C–H/X-H
insertion
migratory
of
carbenes.
In
this
presentation,
the
racemic
synthesis
important
ligand
like
8-azaBINOL
and
phosphine
ligands
QUINAP,
METHOX,
PINAP,
PHENAP
will
be
discussed
[2,3].
Construction
indolocoumarin,
especially
isolamellarins,
using
quinoid
carbene
explained
[4].
A
straightforward
Rh(III)-catalyzed
method
for
introduction
naphthol/phenol
C(sp3)–H
bond
8-methylquinoline
diazonaphthalen-2(1H)-ones/quinone
diazides
[5].
Further,
site-selective
N-arylation
benzotriazole,
2-hydroxy
pyridine
amide
bonds
methods
explored
[6-8].
Next,
a
Ru(II)-catalyzed
construct
O-alkylated
arylnaphthyl
thioether
derivatives
α-thioesters
diazonaphthoquinone
an
unprecedented
[1,4]-oxa
sigmatropic
rearrangement
in
complementary
method,
O-heteroaryl
alkylnaphthyl
concerted
intramolecular
SNAr-type
reaction
[9].
Molecules,
Год журнала:
2024,
Номер
29(17), С. 4032 - 4032
Опубликована: Авг. 26, 2024
Lamellarins
are
natural
products
with
a
[3,4]-fused
pyrrolocoumarin
skeleton
possessing
interesting
biological
properties.
More
than
70
members
have
been
isolated
from
diverse
marine
organisms,
such
as
sponges,
ascidians,
mollusks,
and
tunicates.
There
is
continuous
interest
in
the
synthesis
of
these
compounds.
In
this
review,
synthetic
strategies
for
title
compounds
presented
along
their
Three
routes
followed
lamellarins.
Initially,
pyrrole
derivatives
starting
or
intermediate
compounds,
then
they
fused
to
isoquinoline
coumarin
moiety.
Second,
compound
an
indole
last
route,
coumarins
which
moiety
scaffold.
The
isolamellarins,
azacoumestans,
isoazacoumestans,
analogues
also
described.
above
achieved
via
metal-catalyzed
cross-coupling,
[3
+
2]
cycloaddition,
substitution,
lactonization
reactions.
exhibit
cytotoxic,
multidrug
resistance
(MDR),
topoisomerase
I-targeted
antitumor,
anti-HIV,
antiproliferative,
anti-neurodegenerative
disease,
anti-inflammatory
activities.
Organic Letters,
Год журнала:
2023,
Номер
25(16), С. 2873 - 2877
Опубликована: Апрель 13, 2023
A
Rh(II)-catalyzed
simple
and
efficient
synthesis
of
N-arylated
2-pyridone
derivatives
is
described
using
2-oxypyridine
diazonaphthoquinone
as
coupling
partners.
The
reaction
proceeds
through
the
insertion
nitrogen
atom
derivative
into
quinoid
carbene
subsequent
1,6-benzoyl
migratory
rearrangement.
broadened
with
sufficient
scope
has
potential
to
offer
axially
chiral
under
suitable
asymmetric
conditions.
A
straightforward
synthesis
of
trans-dihydronaphthodioxine
has
been
efficiently
accomplished
through
Cu(II)-NHC
catalysis,
involving
the
stereoselective
ring
opening
cis-epoxides
with
quinoid-carbene.
Intramolecular
SN2-like
substitution
facilitates
inversion
stereochemistry
during
cis-epoxide
opening.
This
reaction
developed
under
simple
conditions,
demonstrating
a
broad
substrate
scope
wide
chemoselective
profile.
Additionally,
late-stage
functionalization
complex
bioactive
molecules
successfully
achieved.
Journal of Medicinal Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 1, 2025
Ischemic
stroke,
a
major
cause
of
disability
and
death
worldwide,
lacks
effective
treatments
due
to
the
complexity
brain
ischemia/reperfusion
(I/R)
injury.
The
transient
receptor
potential
melastatin
2
(TRPM2)
channel
is
promising
therapeutic
target.
In
this
study,
an
extracellular
TRPM2
inhibitor
A1
with
indolizine
scaffold
was
identified
through
chemical
library
screening.
Four
series
derivatives
were
synthesized,
yielding
four
compounds
inhibitory
activity
comparable
or
superior
A1,
as
confirmed
by
calcium
fluorescence
electrophysiological
assays.
These
demonstrated
significant
neuroprotective
effects
in
vitro.
Among
them,
D10
showed
robust
efficacy
reducing
cerebral
infarction
middle
artery
occlusion
(tMCAO)
model,
surpassing
edaravone.
When
administered
24
h
postreperfusion
continued
for
7
days,
exhibited
sustained
vivo
antistroke
improved
survival
rates
compared
edaravone
vehicle
controls.
represents
lead
compound
ischemic
stroke
therapy.
New Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
novel
approach
for
constructing
3,4-difunctionalized
benzo[
h
]coumarins
through
a
metal-free
multicomponent
reactions
with
mild
reaction
conditions.
Chemical Communications,
Год журнала:
2023,
Номер
59(88), С. 13187 - 13190
Опубликована: Янв. 1, 2023
Weakly
coordinating
enaminone
functionality
has
been
leveraged
for
C–H
activation
strategy
under
ruthenium
catalysis
the
regioselective
annulative
coupling
of
arenes
with
diazonaphthoquinones,
offering
polycyclic
benzocoumarins
in
high
yields.
Organic Letters,
Год журнала:
2022,
Номер
24(46), С. 8470 - 8475
Опубликована: Ноя. 14, 2022
A
rhodium(III)-catalyzed
Satoh-Miura
type
oxidative
annulation
of
N-aryl
2-pyridone
derivatives
is
described
using
internal
alkyne
as
a
coupling
partner.
weakly
coordinating
carbonyl
group
the
ring
utilized
for
this
transformation.
The
reaction
proceeds
with
broad
scope
and
wide
functional
tolerance.
solvent
plays
an
important
role
in
developed
method
to
furnish
different
class
annulated
product.
preliminary
investigation
was
carried
out
explore
photophysical
properties
obtained
polyarylated
N-naphthyl
2-pyridones.
