Advanced Synthesis & Catalysis,
Journal Year:
2019,
Volume and Issue:
361(8), P. 1896 - 1901
Published: Feb. 11, 2019
Abstract
An
efficient
method
for
the
synthesis
of
substituted
1(2
H
)‐isoquinolone
derivatives
via
nickel‐catalyzed
annulation
2‐halobenzamidines
with
aryl
alkynes
in
presence
water
is
described.
Benzo[4,5]imidazo[2,1‐
a
]isoquinolines
were
formed
as
dominated
products
when
dry
dimethyl
sulfoxide
was
used
solvent.
Furthermore,
benzyl
amidines
substrates,
debenzylation
reaction
occured
to
provide
various
1‐aminoisoquinoline
products.
magnified
image
The Journal of Organic Chemistry,
Journal Year:
2017,
Volume and Issue:
82(20), P. 11182 - 11191
Published: Sept. 28, 2017
An
efficient
one-pot
indole-to-carbazole
strategy
with
cyclohexanones
as
the
aryl
source
is
described.
This
cascade
carbazole
formation
enabled
by
NH4I-catalyzed
annulation
of
indoles,
cyclohexanones,
and
alkenes
subsequent
dehydrogenative
aromatization.
The
present
work
provides
a
modular
synthesis
arylcarbazoles,
benzocarbazoles,
naphthocarbazoles
excellent
regioselectivity
broad
functional
group
tolerance.
More
than
40
benzo-fused
carbazoles
were
synthesized,
UV-vis
absorption
photoluminescent
spectra
some
products
measured
to
study
their
photophysical
properties.
Organic Letters,
Journal Year:
2018,
Volume and Issue:
20(12), P. 3451 - 3454
Published: May 31, 2018
An
unexpected
FeCl3-catalyzed
cascade
reaction
of
simple
indoles
and
o-hydroxychalcone
was
reported,
leading
to
densely
functionalized
strained
chromane-bridged
polycyclic
in
moderate
good
yields.
This
not
only
establishes
a
new
transformation
o-hydroxychalcones
but
also
provides
an
efficient
method
for
the
synthesis
structurally
complex
congested
indoles.
Organic Letters,
Journal Year:
2018,
Volume and Issue:
20(21), P. 6920 - 6924
Published: Oct. 25, 2018
A
one-pot,
protecting-group-free
benzannulation
of
2-alkenylindoles
with
readily
available
1,3-dicarbonyls
is
demonstrated
to
construct
structurally
diverse
carbazoles.
The
use
a
cheap
Brønsted
acid
catalyst
and
air
as
the
sole
oxidant
exemplifies
economic
viability
this
protocol.
execution
four
different
reactions
successively
generate
medicinally
important
indolocarbazole
core
also
achieved.
This
one-pot
method
paved
way
for
total
synthesis
three
alkaloids,
namely
staurosporinone,
arcyriaflavin
A,
7-hydroxy-K252c.
The Journal of Organic Chemistry,
Journal Year:
2017,
Volume and Issue:
82(24), P. 13277 - 13287
Published: Nov. 13, 2017
TfOH-catalyzed
one-pot
sequential
reaction
of
indoles,
acetophenones
(cyclic
ketones),
and
various
3-methyleneoxindolines
in
toluene
afforded
polysubstituted
tetrahydrospiro[carbazole-1,3'-indoline]s
satisfactory
yields.
1H
NMR
spectra
single-crystal
structures
indicated
that
the
obtained
existing
an
unusual
trans-configuration.
The
mechanism
was
believed
to
proceed
with
domino
acid-catalyzed
3-alkenylation
indoles
acetophenones,
Diels-Alder
3-alkyenylindoles
3-methyleneoxindolines,
diastereoisomerization
process.
Advanced Synthesis & Catalysis,
Journal Year:
2018,
Volume and Issue:
360(20), P. 4017 - 4022
Published: Aug. 13, 2018
Abstract
Elemental
sulfur‐promoted
cyclization
for
the
one‐pot
synthesis
of
tetra‐substituted
imidazoles
from
benzylamines
and
ketones
is
described.
sulfur
combined
with
molecular
oxygen
as
benign
co‐oxidant
was
found
to
be
key
high
efficiency
this
transformation
under
metal‐free
conditions.
A
range
tetrasubstituted
were
synthesized
simple
amines
good
functional
group
tolerance.
magnified
image
Organic Letters,
Journal Year:
2017,
Volume and Issue:
19(22), P. 6140 - 6143
Published: Nov. 2, 2017
An
N-bromosuccinimide-catalyzed
intermolecular
annulation
of
acetyl
indoles
with
alkynes
was
developed,
allowing
for
regioselective
formation
valuable
carbazoles
through
direct
C-H
bond
functionalization.
The
readily
available
catalyst,
wide
substrate
scope,
gram
scale
synthesis,
and
mild
conditions
make
this
method
practical.
Mechanistic
investigations
indicate
that
the
bromination
indole
takes
place
to
generate
a
bromide
intermediate,
followed
by
coupling
an
alkyne
intramolecular
cycloaromatization
furnish
carbazole
products.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(8), P. 5616 - 5629
Published: April 5, 2021
A
simple
InBr3-catalyzed
domino
reaction
of
indoles,
phenylacetylenes,
and
various
3-methyleneoxindolines
in
toluene
is
described.
This
not
only
provided
a
convenient
synthetic
protocol
for
polysubstituted
tetrahydrospiro[carbazole-1,3′-indolines]
good
yields
but
also
gave
completely
different
diastereoisomers
the
to
that
previously
reported
TfOH-catalyzed
one-pot
acetophenones,
3-methyleneoxindolines.
Additionally,
initially
prepared
1,1′-bis(indolyl)phenylethanes
with
3-phenacylideneoxindolines
corresponding
excellent
diastereoselectivity.
The
mechanism
involved
sequential
situ
generation
reactive
dienophilic
3-alkenylindole,
Diels–Alder
reaction,
Lewis
acid
controlled
diastereoisomerization
process.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(4), P. 884 - 891
Published: Jan. 3, 2024
Abstract
Polysubstituted
carbazoles
were
efficiently
synthesized
through
direct
benzannulation
reaction
between
1,4‐dicarbonyl
compounds
and
indoles
with
catalytic
amount
of
inexpensive
zirconium(IV)
chloride.
This
transformation
proved
to
be
regioselective
furnishes
1,4‐disubstituted
1,2,4‐trisubstituted
yields
ranging
from
26%
91%
broad
substrate
scope.
Moreover,
this
protocol
benefits
using
readily
accessible
starting
materials
without
the
need
their
pre‐functionalization.
The
synthetic
utility
products
was
exemplified
by
functionalization
an
iodocarbazole
means
Suzuki‐Miyaura
reactions
synthesis
a
3‐deaza‐derivative
natural
product
canthin‐6‐one.
RSC Advances,
Journal Year:
2025,
Volume and Issue:
15(13), P. 9676 - 9755
Published: Jan. 1, 2025
The
tremendous
potential
of
transition
metal-free
multi-component
reactions
(MCR)
in
the
synthesis
N-heterocyclic
frameworks
is
examined
this
review,
offering
a
complete
overview
subject
matter.
discussion
on
mechanistic
rationale
reaction
routes
and
intermediates
provides
profound
insights
into
underlying
changes,
encouraging
deeper
investigation
various
molecular
frameworks.
This
review
serves
as
doorway
to
study
practicality
exploiting
these
for
efficient
uncomplicated
specific
nitrogen
heterocycles.
Specifically,
we
reveal
catalysts
field.
Because
their
extensive
scope
diversity,
enable
heterocycles
that
contain
nitrogen,
which
include
5-membered
(carbazole,
pyrimidines,
pyrroles)
6-membered
rings
(piperidine,
pyridine,
quinoline,
diazinane,
pyrazine,
quinoxaline,
1,2,3-triazine).
In
addition,
compatibility
with
functional
groups
substrates
not
only
increases
synthetic
value
compounds
but
also
broadens
relevance
domains
medical
chemistry,
materials
science,
other
relevant
areas
study.
To
motivate
future
development
field,
successful
examples
described
highlight
powerful
instruments
quick
general,
thorough
insightful
examination
catalysts,
highlighting
contemporary
organic
revolutionize
field
heterocycle
synthesis.
