Chemistry - An Asian Journal,
Journal Year:
2024,
Volume and Issue:
19(22)
Published: July 16, 2024
Abstract
Over
the
decades,
functionalized
heteroaromatic
compounds
and
their
scaffolds
have
drawn
significant
attention
in
synthetic
organic
chemistry
as
well
interdisciplinary
sciences
due
to
prevalence
natural
products,
hormones,
vitamins,
applications
pharmaceuticals,
agrochemicals,
veterinary
dyes
pigments,
bio‐imaging,
semiconductors,
optoelectronics,
etc.
This
review
explores
various
strategies
for
functionalization
of
numerous
5,6
benzo‐fused
derivatives
such
indole,
benzofuran,
benzothiophene,
benzimidazole,
benzoxazole,
benzothiazole
benzotriazole
through
methods
including
C−H
activation,
cross‐coupling,
metal
catalysis,
photo‐catalysis,
electrocatalysis
organocatalysis
recent
years
(2019–2023).
Highly
heterocyclic
are
important
precursors
synthesizing
many
bioactive
drugs
like
fenbendazole,
viozan,
griseofulvin,
zileuton,
flunoxaprofen,
optoelectronic
materials,
Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
144(16), P. 7072 - 7079
Published: March 22, 2022
The
2,3-dihydrobenzofuran
scaffold
is
widely
found
in
natural
products
and
biologically
active
compounds.
Herein,
dearomatizing
2,3-fluoroaroylation
of
benzofurans
with
aroyl
fluorides
as
bifunctional
reagents
to
access
2,3-difunctionalized
dihydrobenzofurans
reported.
reaction
that
occurs
by
cooperative
NHC/photoredox
catalysis
provides
3-aroyl-2-fluoro-2,3-dihydrobenzofurans
moderate
good
yield
high
diastereoselectivity.
Cascades
proceed
via
radical/radical
cross-coupling
a
benzofuran
radical
cation
generated
the
photoredox
cycle
neutral
ketyl
formed
through
NHC
cycle.
redox-neutral
transformation
exhibits
broad
substrate
scope
functional
group
compatibility.
With
anhydrides
reagents,
aroyloxyacylation
achieved
strategy
can
also
be
applied
Chemistry - An Asian Journal,
Journal Year:
2023,
Volume and Issue:
18(9)
Published: March 15, 2023
Electrochemical
dearomative
spirocyclization
serves
as
a
green
and
sustainable
approach
to
convert
the
flat,
two-dimension
aromatic
feedstock
into
value-added
three-dimension
spirocyclic
architectures.
This
review
highlights
recent
advances,
emphasizes
mechanistic
discussions,
showcases
synthetic
applications
of
this
emerging
versatile
powerful
transformation.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(16), P. 9326 - 9333
Published: April 13, 2023
We
report
that
the
dearomative
[4
+
2]
cycloaddition
between
1,2-dihydro-1,2,4,5-tetrazine-3,6-diones
(TETRADs)
and
benzenes,
naphthalenes,
or
N-heteroaromatic
compounds
under
visible
light
irradiation
affords
corresponding
isolable
cycloadducts.
Several
synthetic
transformations
including
transition-metal-catalyzed
allylic
substitution
reactions
using
isolated
cycloadducts
at
room
temperature
above
were
demonstrated.
Computational
studies
revealed
retro-cycloaddition
of
benzene–TETRAD
adduct
proceeds
via
an
asynchronous
concerted
mechanism,
while
benzene–MTAD
(MTAD
=
4-methyl-1,2,4-triazoline-3,5-dione)
a
synchronous
mechanism.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(4), P. 866 - 871
Published: Jan. 25, 2024
In
this
study,
we
report
a
transfer
hydrogenation
protocol
that
utilizes
borane–ammonia
(H3N–BH3)
as
the
hydrogen
source
and
commercially
available
RuCl3·xH2O
precatalyst
for
selective
aromatic
reduction
of
quinolines,
quinoxalines,
pyridines,
pyrazines,
indoles,
benzofurans,
furan
derivatives
to
form
corresponding
alicyclic
heterocycles
in
good
excellent
isolated
yields.
Applications
straightforward
include
efficient
preparation
useful
key
pharmaceutical
intermediates,
such
donepezil
flumequine,
including
biologically
active
compound.
ACS Sustainable Chemistry & Engineering,
Journal Year:
2023,
Volume and Issue:
11(35), P. 13142 - 13148
Published: Aug. 24, 2023
Benzothiazolines,
with
their
versatile
nature,
serve
as
fundamental
building
blocks
for
the
synthesis
of
significant
biological
compounds.
However,
methods
preparation
benzothiazolines
from
readily
available
starting
materials
are
limited.
An
efficient
benzothiazoline
via
photoredox-catalyzed
dearomatization
benzothiazole
derivatives
has
been
achieved
at
room
temperature.
This
catalysis
proceeds
a
ligand
to
metal
charge
transfer
process,
and
FeCl3
plays
dual
role
an
indirect
HAT
reagent
reducing
agent.
methodology
can
be
conveniently
scaled
up,
most
alkylated
products
purified
without
chromatography.
In
addition,
this
process
exhibited
advantages
low
cost,
high
reaction
efficiency,
mild
conditions.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(34), P. 6321 - 6325
Published: Aug. 22, 2022
The
Friedel–Crafts
type
alkylation
of
C2-tethered
thiophenes
has
been
reported
to
be
nonregioselective.
Taking
advantage
the
highly
regioselective
5-exo-trig
spirocyclization
an
electrochemically
generated
amidyl
radical,
we
have
unraveled
electrochemical
dearomative
N-acyl
thiophene-2-sulfonamides.
Various
nucleophilic
agents,
including
carboxylates,
alcohols,
and
fluoride,
are
readily
incorporated
afford
remotely
functionalized
spirocyclic
dihydrothiophenes,
their
novel
scaffolds
shown
exhibit
promising
antitumor
activities.
European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
2022(18)
Published: April 5, 2022
Abstract
Dearomatization
reactions
employing
simple
aromatic
compounds
have
showcased
remarkable
progress
in
the
recent
decade
and
emerged
as
one
of
most
straightforward
powerful
tools
for
creation
highly
functionalized,
three‐dimensional
molecular
frameworks
commonly
encountered
medicinal
chemistry
life
sciences.
Among
use,
nitro(hetero)arenes,
which
feature
a
less
pronounced
character
due
to
presence
electron‐withdrawing
nitro
group,
been
extensively
used
different
types
dearomatization
reactions.
The
dearomative
annulation
reaction
serves
versatile
method
construction
complex
polycyclic
systems.
This
overview
presents
brief
summary
impressive
advances
nitro(hetero)arenes
provides
some
inspirations
future
research.
Arabian Journal of Chemistry,
Journal Year:
2023,
Volume and Issue:
16(8), P. 104975 - 104975
Published: May 13, 2023
This
study
was
conducted
to
synthesize
and
characterize
a
new
polymer/metal–organic
framework
(MOF)
stabilizer
via
the
reaction
between
sulfonamide-triazine-based
porous
organic
polymer
(poly(sulfonamide-triazine))
(PSTA)
an
amino-functionalized
zinc
metal–organic
(IRMOF-3).
Next,
prepared
nanocomposites
(IRMOF-3/PSTA/Cu)
were
modified
using
copper
iodide
nanoparticles
(CuI
NPs).
The
composites
characterized
by
FT-IR,
XRD,
EDX,
N2
adsorption–desorption,
TGA,
SEM,
TEM,
XPS
analysis.
Finally,
application
of
investigated
through
one-pot
synthesis
2,3-disubstituted
benzo[b]furans.
To
this
end,
alkyne,
salicylaldehydes,
amines
subjected
three-component
domino
reaction.
All
products
obtained
in
high
turnover
frequency
(TOF)
up
142.42,
suggesting
catalyst's
selectivity
activity
mentioned
reactions.
synthesized
nanocatalyst
is
reusable
seven
times
with
no
considerable
catalytic
efficiency
loss.
Overall,
yields
products,
nanocatalyst's
facile
recovery,
short
time,
wide
substrate
scopes
make
procedure
eco-friendly,
practical,
economically
justified.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(31), P. 5829 - 5834
Published: July 30, 2022
A
novel
method
toward
a
facile
synthesis
of
diverse
benzofuran
derivates
from
easily
obtained
quinols
and
alkynyl
esters
has
been
reported.
gold-catalyzed
intermolecular
alkoxylation/Claisen
rearrangement/condensation
cascade
was
involved.
The
introduction
difluorodiphenylsilane
as
water-trapping
reagent
in
the
reaction
leads
to
higher
yield.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(12), P. 3322 - 3327
Published: Jan. 1, 2022
The
higher-order
[10
+
2]
cycloaddition
of
3-nitroindoles
and
2-alkylidene-1-indanones
enables
the
dearomatization
affords
a
range
structurally
diverse
cyclopenta[
b
]indolines
with
excellent
results.
