Abstract
A
simple
and
beneficial
strategy
for
the
construction
of
2,3‐dihydrofurans
from
α‐bromochalcones
α‐substituted
cyanoketones
via
Michael
addition‐alkylation
reaction
has
been
realized.
This
transformation
was
well
compatible
with
various
cyanoketones,
corresponding
multifunctionalized
were
obtained
in
up
to
98
%
yield.
highly
diastereoselective
variant
also
developed.
Moreover,
could
be
performed
on
gram‐scale.
Frontiers in Chemistry,
Год журнала:
2024,
Номер
12
Опубликована: Фев. 19, 2024
This
comprehensive
review,
covering
2021-2023,
explores
the
multifaceted
chemical
and
pharmacological
potential
of
coumarins,
emphasizing
their
significance
as
versatile
natural
derivatives
in
medicinal
chemistry.
The
synthesis
functionalization
coumarins
have
advanced
with
innovative
strategies.
enabled
incorporation
diverse
functional
fragments
or
construction
supplementary
cyclic
architectures,
thereby
biological
physico-chemical
properties
compounds
obtained
were
enhanced.
unique
structure
coumarine
facilitates
binding
to
various
targets
through
hydrophobic
interactions
pi-stacking,
hydrogen
bonding,
dipole-dipole
interactions.
Therefore,
this
important
scaffold
exhibits
promising
applications
uncountable
fields
chemistry
(e.g.,
neurodegenerative
diseases,
cancer,
inflammation).
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(8), С. 1744 - 1750
Опубликована: Фев. 22, 2024
Abstract
The
transmetalation
triggered
rhodium‐catalyzed
C−H
bond
activation
and
tandem
annulation
of
2‐biphenylboronic
acids
with
sulfoxonium
ylides
or
iodonium
has
been
developed.
Various
products
phenanthrenes
were
constructed
under
redox‐neutral
conditions
in
34–86%
yields.
Several
mechanism
exploration
experiments
derivatization
reactions
conducted
sequence
to
gain
a
deeper
understanding
the
process
potential
this
transformation.
It
offers
an
alternative
approach
for
synthesis
phenanthrene
derivatives.
RSC Advances,
Год журнала:
2024,
Номер
14(21), С. 14539 - 14581
Опубликована: Янв. 1, 2024
The
synthesis
of
dihydrobenzofuran
scaffolds
bears
pivotal
significance
in
the
field
medicinal
chemistry
and
organic
synthesis.
These
heterocyclic
hold
immense
prospects
owing
to
their
significant
pharmaceutical
applications
as
they
are
extensively
employed
essential
precursors
for
constructing
complex
frameworks.
Their
versatility
importance
make
them
an
interesting
subject
study
researchers
scientific
community.
While
exploring
synthesis,
have
unveiled
various
novel
efficient
pathways
assembling
core.
In
wake
extensive
data
being
continuously
reported
each
year,
we
outlined
recent
updates
(post
2020)
on
methodological
accomplishments
employing
catalytic
role
several
transition
metals
forge
functionalities.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
90(4), С. 1645 - 1655
Опубликована: Янв. 17, 2025
We
present
a
novel,
metal-
and
additive-free
method
for
the
robust
synthesis
of
dihydrofuran-fused
naphthalenes
coumarins.
This
approach
utilizes
annulative
coupling
sulfoxonium
ylides
with
aldehydes,
naphthols,
or
coumarins
at
ambient
temperature.
The
exhibits
broad
substrate
compatibility,
accommodating
various
functional
groups
on
naphthol
coumarin
derivatives
resulting
in
good
to
high
yields
desired
products.
Additionally,
we
successfully
scaled
up
reactions,
synthesized
were
further
converted
other
valuable
bioactive
molecules,
validating
viability
our
approach.
A
three-component
multi-auto-tandem
reaction
for
the
construction
of
site-specific
tricyclic
furo[3,2-c]coumarins
via
formation
C-C,
C-O,
and
C-S
bonds
in
one
step
from
4-hydroxycoumarins/4-hydroxy-2-pyrones,
ynals,
sodium
sulfinates
is
reported.
This
cascade
efficiently
produces
a
variety
rare
C-2-functionalized
moderate
to
good
yields
under
straightforward
conditions.
Furthermore,
this
protocol
can
be
extended
coupling
involving
2-hydroxy-1,4-naphthoquinone,
sulfinates,
yielding
naphtho[2,3-b]furan-4,9-dione
derivatives.
Notably,
carbonyl
group
α-position
ynals
act
as
C-2
synthons
specific
reaction,
enabling
two
aforementioned
types
multicomponent
transformations.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(27), С. 5567 - 5586
Опубликована: Янв. 1, 2023
Efficacious
protocols
have
been
established
to
synthesize
a
structurally
privileged
Π-extended
coumarin-fused
pyridone
nucleus
by
activating
the
vinylic
C(sp2)-H
bond
of
coumarin-3-carboxamide
under
influence
inexpensive
Ru(II)-metal.
Here
an
N-methoxy
carboxamide
entity
has
exploited
as
chelating
fragment
manifest
functionalization
with
concomitant
(4
+
2)
annulation
reaction,
resulting
in
heterocyclic
ring-forming
along
sulfoxonium
ylide
and
iodonium
representative
bench-stable
carbene
surrogates.
This
diverse
heterocycle
formation
via
insertion
strategies,
is
further
expanded
activate
ortho-C(sp2)-H
bonds
different
heterocycles
employing
sp2-N
moiety
directing
group
develop
acyl-alkylated/alkenylated
quinazolines,
isoxazoles
highly
fluorescent
pyridone-N-oxides.
Intriguingly,
during
evaluation
versatility
current
protocols,
one-pot
double
C-H
activation
rationalized
presence
ylide,
which
results
biologically
potent
benzimidazole-fused
coumarin-centered
bridge-headed
polycyclic
heteroarenes.
Furthermore,
chemo-selective
late-stage
synthetic
transformation
being
designed
differently
substituted
analogues
switching
nature
reducing
agent.
In
addition,
photophysical
experiment
was
done
on
one
pyridine-N-oxide
compound
(7e)
delightfully
it
exhibited
fluorescence
quenching
activity
selectively
Al3+
ions,
appears
be
unique
feature
our
methodology.
Finally,
upon
correlation
merit
developed
pathways,
mediated
strategy
superior.
Organic Letters,
Год журнала:
2023,
Номер
25(24), С. 4493 - 4497
Опубликована: Июнь 9, 2023
An
efficient
and
fascinating
protocol
has
been
devised
for
the
preparation
of
fused
furan
moieties
involving
a
Rh(II)
catalyzed
one-pot
C–H
activation/concomitant
tandem
annulation
process,
employing
an
enolic
compound
β-keto
sulfoxonium
ylide
as
reacting
conjugates.
The
developed
technique
demands
only
Rh2(TFA)4
catalyst
to
proceed
forward
is
devoid
additional
metallic
or
nonmetallic
additives.
skeletal
transformation
naphthoquinone
highly
decorated
indolizines
promising
synthetic
application.
Chemical Communications,
Год журнала:
2023,
Номер
59(78), С. 11704 - 11707
Опубликована: Янв. 1, 2023
Ru(
ii
)-catalyzed
condition-controlled
divergent
coupling
between
3-aryl-2
H
-benzoxazin-2-ones
and
benzoquinones
has
been
realized
under
operationally
simple
conditions,
affording
a
series
of
structurally
stable
spiropyrans
valuable
arylquinones.
