Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(27), P. 5657 - 5663
Published: June 28, 2024
A
protocol
for
the
electrooxidative
[3+2]
annulation
to
generate
indolo[2,3-b]indoles
in
an
undivided
cell
is
reported.
It
exhibits
good
yields
with
excellent
regioselectivities
and
tolerates
various
functional
groups
without
external
chemical
oxidants.
Cyclic
voltammetry
density
theory
calculations
indicate
that
initiated
by
simultaneous
anodic
oxidation
of
indole
aniline
derivatives,
step
determine
rate
relies
on
combination
radical
cations.
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 25, 2025
The
direct
conversion
of
o-cresol
and
2-methylphenols
to
2-methylbenzofurans
was
achieved
by
an
Ir/DTBE-DPPE-catalyzed
reaction
under
atmosphere
ethylene
(1
atm).
involves
the
initial
selective
formation
a
C-C
bond
at
benzylic
C(sp3)-H
with
without
accommodation
C(sp2)-H
bonds
6-positions,
which
is
followed
subsequent
C-O
bond-forming
annulation
along
associated
dehydrogenation
double
migration
steps.
conditions
also
allowed
for
o-toluidine
2-methylanilines
into
2-methylindoles.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(14), P. 10027 - 10039
Published: July 11, 2023
We
have
developed
a
direct
method
for
the
synthesis
of
polyring-fused
imidazo[1,2-a]pyridines
via
copper-catalyzed
annulation
electrophilic
benzannulated
heterocycles
with
2-aminopyridine
and
2-aminoquinoline.
From
3-nitroindoles
2-aminopyridine,
we
could
synthesize
tetracenes,
viz.,
indole-fused
imidazo[1,2-a]pyridines,
by
starting
from
2-aminoquinoline,
generate
pentacenes,
indolo-imidazo[1,2-a]quinolines.
In
addition,
also
extend
methodology
toward
benzothieno-imidazo[1,2-a]pyridines
3-nitrobenzothiophene.
Furthermore,
basic
photophysical
properties
these
synthesized
heteroacenes
were
evaluated.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(14), P. 9877 - 9892
Published: July 12, 2023
We
have
come
across
a
substrate
namely,
5-benzoyl-pyrrolo[2,1-a]isoquinoline
in
which
three
different
functionalizable
C–H
bonds
were
identified
that
could
be
judiciously
transformed
site
selectively
for
the
generation
of
complex
polyring
fused
N-heterocycles.
A
Pd-catalyzed
cross-dehydrogenative
coupling
afforded
8H-indeno-pyrrolo[2,1-a]isoquinolinone
and
an
oxygen
induced
palladium
catalyzed
selective
amination
same
provided
pentacene
viz.,
9H-indolo-pyrrolo[2,1-a]isoquinoline.
also
observed
formation
multiring
benzazepine
scaffold
by
5-(4-nitro
benzoyl)-pyrrolo[2,1-a]isoquinoline.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(10)
Published: Jan. 25, 2024
Abstract
Heteroacenes
are
considered
as
an
important
class
of
compounds
for
material
applications
due
to
their
stability,
electron‐richness
and
tunable
properties.
Mostly,
four
ring
containing
heteroacenes
have
found
immense
in
organic
electronic
devices
some
them
been
successfully
commercialized.
One
such
heteroacene
benzothienobenzofuran
which
different
isomers
reported
date
based
on
the
position
where
benzothiophene
unit
is
fused
benzofuran
ring.
The
available
literature
claims
synthetic
strategies
towards
benzothienobenzofurans
starting
from
multistep
synthesis
tandem
transformations,
electrochemical
annulations.
Different
metal
catalyzed
transformations
including
Pd‐catalyzed
dual
C−H
activations,
Ullmann
coupling,
metal‐catalyzed
one‐pot
processes
etc.
benzothienobenzofurans.
present
review
analyses
all
methodologies
preparation
examines
generality
each
method
by
highlighting
its
advantages
disadvantages.
We
discuss
mechanisms
reactions
benefit
readers.
Finally,
existing
basic
photophysical
properties
limited
fabricating
light‐emitting
diode
(OLED),
field‐effect
transistor
(OFET),
phototransistor
(OPT)
uses
deliberated
Synthesis,
Journal Year:
2024,
Volume and Issue:
unknown
Published: July 4, 2024
Abstract
Domino
reactions
are
essential
for
advancing
organic
synthesis.
This
study
introduces
novel
thioamide-based
precursors
a
palladium-catalyzed
selective
domino
heteroarylation
process.
The
method
efficiently
produces
benzothieno[2,3-b]quinolones
with
yields
ranging
from
moderate
to
very
good.
By
employing
aryl
chlorides,
the
efficiency
of
hetero-annulation
process
is
comparable
that
bromides.
Executing
one-pot,
two-step
reaction
also
delivered
single
product
high
selectivity.
strategy
involved
fine-tuning
substituent
reactivity,
utilizing
electron-rich
arenes,
and
forming
metallocycles
nucleophilic
sulfur,
consistently
yielding
product.
proposed
mechanism
corroborated
by
mechanistic
studies.
European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
26(4)
Published: Dec. 19, 2022
Abstract
One‐pot
synthesis
of
various
indolo[2,3‐
b
]indoles
has
been
accomplished
from
a
copper‐catalyzed
transformation
easily
accessible
2‐(substituted‐amino)aryl)(mesityl)iodonium
salts
and
indole
derivatives.
Reaction
offers
great
functional
group
toleration,
providing
series
]indole
derivatives
in
good
yields.
Additionally,
intramolecular
cyclization
the
presence
copper‐catalyst
provided
direct
access
to
benzoxazole
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(13), P. 1674 - 1689
Published: Jan. 1, 2024
This
feature
article
describes
the
different
annulation
strategies
with
electrophilic
benzannulated
heterocycles
for
accessing
heteroacenes
(polyring
fused
heterocycles)
reported
from
1996
to
date.
