Organic Letters,
Год журнала:
2017,
Номер
19(22), С. 6140 - 6143
Опубликована: Ноя. 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.
Organic Letters,
Год журнала:
2018,
Номер
20(14), С. 4285 - 4289
Опубликована: Июль 6, 2018
A
three-component
reaction
of
indoles,
α-bromoacetaldehyde
acetals,
and
ketones
was
developed
by
using
bismuth(III)
triflate
as
the
catalyst
to
realize
a
straightforward
approach
for
synthesizing
carbazole
derivatives.
The
established
mechanistically
through
autotandem
catalysis
Bi(OTf)3
in
following
two
steps:
(i)
Friedel–Crafts-type
alkylation
indole
with
acetal,
which
produced
tryptaldehyde-type
intermediate
(ii)
[4
+
2]
annulation
this
ketone
component.
Advanced Synthesis & Catalysis,
Год журнала:
2017,
Номер
359(11), С. 1860 - 1866
Опубликована: Апрель 13, 2017
Abstract
Benzannulation
of
2‐alkenylindoles
with
readily
available
aldehydes,
under
one‐pot
sequential
triple‐relay‐catalysis,
provides
an
easy
access
to
several
structurally
unique
carbazoles
including
2‐
and
3‐alkenylcarbazoles.
This
protecting
group‐free
method
enabled
synthesis
alkaloids
such
as
hyellazole
6‐chlorohyellazole,
the
formal
syntheses
seven
other
alkaloids.
Construction
core
structure,
present
in
murastifoline
A,
murrafoline
E,
related
was
also
demonstrated.
Even
conjugated
3,3′‐biscarbazoles
can
be
synthesized
by
one‐pot,
two‐fold
triple‐relay
catalysis
.
magnified
image
Organic & Biomolecular Chemistry,
Год журнала:
2019,
Номер
18(1), С. 163 - 168
Опубликована: Дек. 2, 2019
The
CuSO4
catalyzed
three-component
reaction
of
indole-2-acetate,
aromatic
aldehydes
and
3-methyleneoxindoles
in
toluene
at
130
°C
afforded
polysubstituted
spiro[carbazole-3,3'-indolines]
good
yields
with
high
diastereoselectivity.
When
isatylidene
malononitriles
were
used
as
dienophiles,
regio-isomeric
spiro[carbazole-2,3'-indolines]
selectively
obtained.
A
similar
2-arylidene-1,3-indanediones
resulted
spiro[carbazole-3,2'-indenes]
satisfactory
stereochemistry
the
diastereoisomers
spiro
compounds
was
clearly
elucidated
by
analysis
NMR
spectra
determination
fourteen
single
crystal
structures.
mechanism
included
formation
reactive
2,3-dimethyleneindoline
a
sequential
Diels-Alder
reaction.
Organic Letters,
Год журнала:
2019,
Номер
21(10), С. 3518 - 3522
Опубликована: Май 6, 2019
An
efficient
three-component
benzoselenophenes
formation
has
been
developed
from
substituted
indoles,
acetophenones,
and
selenium
powder
under
metal-free
conditions.
2-Aryl
indoles
played
an
important
role
to
promote
benzoselenophene
acetophenone
derivatives
powder.
One
C–C
two
C–Se
bonds
were
selectively
formed
provide
40
new
in
good
yields.
Green Synthesis and Catalysis,
Год журнала:
2021,
Номер
2(1), С. 78 - 81
Опубликована: Янв. 22, 2021
A
convenient
method
for
the
rapid
construction
of
indolo[2,3-b]indoles
has
been
developed.
This
cascade
reaction
involving
condensation,
dehydroaromatization,
and
oxidative
annulation
was
achieved
in
a
one-pot
TMSI/DMSO
system,
providing
diversity
functionalized
satisfactory
yields
under
facile
metal-free
conditions.
The
present
protocol
provides
straightforward
approach
to
access
structurally
valuable
indolo[2,3-b],
indoles.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(45), С. 8956 - 8974
Опубликована: Янв. 1, 2023
This
review
discusses
last
decade's
developments
in
carbazole
synthesis.
Aspects
of
selectivity
and
functional
group
tolerance
are
evaluated,
as
well
the
applicability
such
protocols
towards
total
synthesis
natural
products.
The Journal of Organic Chemistry,
Год журнала:
2017,
Номер
82(20), С. 11182 - 11191
Опубликована: Сен. 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,
Год журнала:
2018,
Номер
20(21), С. 6920 - 6924
Опубликована: Окт. 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.
