The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(14), С. 9263 - 9279
Опубликована: Июль 1, 2021
p-TsOH
catalyzed
Diels–Alder
reaction
of
2-(1-alkylindol-3-yl)naphthalene-1,4-diones
and
3-phenacylideneoxindoles
showed
fascinating
diastereoselectivity.
The
with
the
hydrated
afforded
trans-isomers
dihydrospiro[indoline-3,6′-naphtho[2,3-c]carbazoles]
as
major
products.
Alternatively,
anhydrous
under
a
Dean
Stark
apparatus
predominately
gave
cis-isomer
dihydrospiro[indoline-3,6′-naphtho[2,3-c]carbazoles].
On
other
hand,
similar
2-(indol-3-yl)naphthalene-1,4-diones
3-arylideneindolin-2-ones
cis/trans-isomers
Additionally,
2-arylidene-1,3-indanediones
expected
spiro[indene-2,6′-naphtho[2,3-c]carbazoles]
in
satisfactory
yields.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(4), С. 884 - 891
Опубликована: Янв. 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.
Asian Journal of Organic Chemistry,
Год журнала:
2018,
Номер
7(4), С. 711 - 714
Опубликована: Янв. 31, 2018
Abstract
A
one‐pot
synthesis
of
4‐quinolones
starting
from
indoles
is
disclosed.
This
cascade
reaction
involves
a
photocatalytic
aerobic
oxidation
using
visible
light
and
subsequent
base‐promoted
Camps
cyclization.
The
advantages
the
present
protocol
include
use
environmentally
benign
inexpensive
oxygen
as
sole
oxidant,
easy
handling
at
room
temperature,
well
step‐
atom‐economy.
Organic Letters,
Год журнала:
2019,
Номер
21(10), С. 3687 - 3691
Опубликована: Апрель 30, 2019
A
metal-free
strategy
for
the
synthesis
of
benzocarbazoles
from
2-arylindoles
and
aryl
ketones
is
developed.
Various
2-aryl-3-vinyl-indoles
were
generated
in
situ
through
dehydrative
condensation
indoles.
These
key
intermediates
could
be
selectively
converted
into
corresponding
benzo[a]carbazoles
via
a
direct
cyclization
process
between
two
Csp2–H
bonds.
Furthermore,
terminal
alkynes
also
used
as
versatile
C2
source
to
afford
products
good
yields.
Advanced Synthesis & Catalysis,
Год журнала:
2019,
Номер
361(8), С. 1896 - 1901
Опубликована: Фев. 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,
Год журнала:
2021,
Номер
86(14), С. 9263 - 9279
Опубликована: Июль 1, 2021
p-TsOH
catalyzed
Diels–Alder
reaction
of
2-(1-alkylindol-3-yl)naphthalene-1,4-diones
and
3-phenacylideneoxindoles
showed
fascinating
diastereoselectivity.
The
with
the
hydrated
afforded
trans-isomers
dihydrospiro[indoline-3,6′-naphtho[2,3-c]carbazoles]
as
major
products.
Alternatively,
anhydrous
under
a
Dean
Stark
apparatus
predominately
gave
cis-isomer
dihydrospiro[indoline-3,6′-naphtho[2,3-c]carbazoles].
On
other
hand,
similar
2-(indol-3-yl)naphthalene-1,4-diones
3-arylideneindolin-2-ones
cis/trans-isomers
Additionally,
2-arylidene-1,3-indanediones
expected
spiro[indene-2,6′-naphtho[2,3-c]carbazoles]
in
satisfactory
yields.
