Asian Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
10(10), P. 2632 - 2637
Published: Aug. 24, 2021
Abstract
The
concentrated
hydrochloride
catalyzed
reaction
of
3‐(indol‐3‐yl)maleimides
with
(
E
)‐4‐arylidene‐5‐methyl‐2‐phenylpyrazol‐3‐ones
in
acetonitrile
at
room
temperature
afforded
unexpected
Michael
addition
product
high
yields,
which
could
be
easily
converted
to
the
cis/trans
‐diastereoisomers
spiro[pyrazole‐4,5′‐pyrrolo[3,4‐
c
]carbazoles]
nearly
2
:
1
ratios
by
further
oxidation
DDQ.
On
other
hand,
similar
one‐pot
two‐step
)‐5‐arylidene‐2‐phenylthiazol‐4‐one
predominately
gave
cis
spiro[pyrrolo[3,4‐
]carbazole‐5,5′‐thiazoles]
satisfactory
yields.
mechanism
included
domino
acid
and
DDQ
oxidative
coupling
process
ChemistrySelect,
Journal Year:
2025,
Volume and Issue:
10(13)
Published: March 28, 2025
Abstract
A
simple,
expedient
continuously
scalable
flow
chemistry
synthesis
of
a
range
1,4‐dimethylcarbazoles
from
substituted
indoles
and
2,5‐hexanedione
in
the
presence
K‐10
(montmorillonite
clay)
is
reported.
Optimization
conditions
led
to
development
an
in‐house
K‐10/sand
Omnifit
TM
catalyst
column
that
at
140
°C
0.4
mL.min
−1
afforded
>90%
conversion
selected
indole
desired
1,4‐carbazole.
This
equates
ca
80
mg.h
production
rate.
The
reaction
was
tolerant
electron
donating
but
not
withdrawing
indoles.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(36), P. 7188 - 7215
Published: Jan. 1, 2022
This
review
covers
the
reported
use
of
activated
olefins,
such
as
barbiturate-based
for
synthesis
spirobarbiturate-fused
three-
to
seven-membered
carbo-
and
heterocyclic
rings
through
different
synthetic
strategies.
New Journal of Chemistry,
Journal Year:
2023,
Volume and Issue:
47(14), P. 6694 - 6699
Published: Jan. 1, 2023
The
polycyclic
cyclohepta[
b
]indoles
were
efficiently
obtained
via
a
formal
[4+3]
cycloaddition
and
an
unprecedented
rearrangement
of
the
maleimide
motif
from
C3/C2-position
indole
ring.
European Journal of Inorganic Chemistry,
Journal Year:
2022,
Volume and Issue:
2022(11)
Published: Jan. 20, 2022
Abstract
Herein,
we
report
two
newly
synthesized
salen‐type
ligands,
2,3‐bis((3,5‐di‐tert‐butyl‐2‐hydroxybenzyl)thio)maleonitrile
(
H
2
L
1
)
and
2,3‐bis((3,5‐di‐tert‐butyl‐2‐hydroxybenzyl)amino)malenonitrile
(H
4
,
bearing
different
coordination
sites
(sulfur
vs
amine)
at
maleonitrile
tethered
moiety
to
investigate
metal
mediated
non‐innocence
chemistry
of
these
ligands.
Upon
metallation,
ligand
did
not
yield
simple
metal‐ligand
complex,
rather
was
split
into
organic
fragments,
dithiolene
(mnt)
2−
phenol
via
C−S
bond
cleavage
wherein
formed
a
stable
complex
[M(mnt)
]
.
The
interpreted
in
terms
strong
p(π)
…
d(π)
interaction
between
that
invoked
the
intramolecular
rearrangement
facilitating
cleavage.
Interestingly,
further
transformed
either
unprecedented
2,4‐di‐tert‐butyl‐6‐methylenecyclohexa‐2,4‐dienone
(i.
e.
spiro
compound;
5
or
2,4‐di‐tert‐butyl‐6‐(hydroxymethyl)phenol
6
depending
on
temperature
reaction
type
ion
used
which
predicted
using
DFT
calculation.
On
other
hand,
combined
experimental
studies
explained
upon
yielded
non‐cleavage
[M(
)]
3
for
M=Cu(II)
M=Ni(II)
slowly
oxidized
−NH−CH
‐(amine)
region
−N=CH−
(imine)
under
aerobic
environment
C−H
activation,
yielding
[Cu
II
(or
[Ni
=oxidatively
dehydrogenated
product
ligand.
Beilstein Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
17, P. 2425 - 2432
Published: Sept. 16, 2021
The
p
-TsOH-catalyzed
Diels–Alder
reaction
of
3-(indol-3-yl)maleimides
with
chalcone
in
toluene
at
60
°C
afforded
two
diastereoisomers
tetrahydropyrrolo[3,4
-c
]carbazoles,
which
can
be
dehydrogenated
by
DDQ
oxidation
acetonitrile
room
temperature
to
give
the
aromatized
pyrrolo[3,4
]carbazoles
high
yields.
On
other
hand,
one-pot
3-(indol-3-yl)-1,3-diphenylpropan-1-ones
chalcones
or
benzylideneacetone
presence
-TsOH
and
resulted
polyfunctionalized
carbazoles
satisfactory
mechanism
included
oxidative
dehydrogenation
corresponding
3-vinylindoles,
their
acid-catalyzed
sequential
aromatization
process.
New Journal of Chemistry,
Journal Year:
2021,
Volume and Issue:
45(34), P. 15423 - 15428
Published: Jan. 1, 2021
Reactive
3-vinylindoles
were
generated
by
in
situ
DDQ
oxidative
dehydrogenation
of
3-(indol-3-yl)-1,3-diphenylpropan-1-ones,
and
underwent
sequential
Diels–Alder
reaction
to
give
novel
heterocyclic
spirocarbazoles.
Beilstein Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
18, P. 796 - 808
Published: July 7, 2022
In
the
presence
of
copper
sulfate,
three-
or
four-component
reactions
2-methylindole,
aromatic
aldehydes
and
various
cyclic
dienophiles
in
refluxing
toluene
afforded
diverse
spirotetrahydrocarbazoles.
This
reaction
is
an
important
development
Levy
by
using
2-methylindole
to
replace
ethyl
indole-2-acetate
successfully
provides
facile
access
polysubstituted
spiro[carbazole-3,3'-indolines],
spiro[carbazole-2,3'-indolines],
spiro[carbazole-3,5'-pyrimidines]
spiro[carbazole-3,1'-cycloalkanes]
satisfactory
yields
with
high
diastereoselectivity.
ChemistrySelect,
Journal Year:
2021,
Volume and Issue:
6(39), P. 10537 - 10541
Published: Oct. 15, 2021
Abstract
The
three‐component
reaction
of
isoquinoline,
dialkyl
but‐2‐ynedioate
and
4‐arylidene‐5‐methyl‐2‐phenylpyrazol‐3‐ones
in
acetonitrile
at
room
temperature
gave
functionalized
spiro[pyrazole‐4,1′‐pyrido[2,1‐
a
]isoquinolines]
satisfactory
yields
with
cis/cis
‐diastereoisomer
as
major
product.
On
the
other
hand,
similar
quinoline
afforded
both
‐
cis/trans
‐isomeric
spiro[pyrazole‐4,4′‐pyrido[1,2‐
]quinolines]
nearly
comparable
yields.
was
finished
situ
generation
Huisgen’
1,4‐dipole,
sequential
Michael
addition
annulation
process.
