Asian Journal of Organic Chemistry,
Год журнала:
2021,
Номер
10(10), С. 2632 - 2637
Опубликована: Авг. 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
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(9), С. 5440 - 5456
Опубликована: Апрель 3, 2023
p-TsOH-catalyzed
cycloaddition
of
various
3-vinylindoles
and
(indol-2-yl)diphenylmethanols
in
acetonitrile
gave
the
functionalized
cyclopenta[b]indoles
good
yields
with
high
diastereoselectivity
via
[3
+
2]
reaction.
More
importantly,
FeCl3-catalyzed
annulation
reaction
afforded
unexpected
cyclohepta[1,2-b:4,5-b']diindoles
satisfactory
yields,
which
a
formal
[4
3]
an
unprecedented
C3/C2
carbocation
rearrangement
were
first
confirmed
by
determination
single-crystal
structure.
European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(46)
Опубликована: Ноя. 16, 2022
Abstract
Spiro
derivatives
are
important
scaffolding
substances
found
in
many
natural
products
and
pharmaceuticals.
In
the
last
decade,
numerous
new
approaches
based
on
multicomponent
reactions
have
been
explored
for
selective
efficient
development
of
spiro
using
various
organocatalytic
transition
metal‐based
catalytic
systems.
This
Review
discusses
pioneering
advances
field
stereoselective
preparation
derivatives.
These
include
Michael
cascade
cyclization
reactions,
cycloadditions,
diastereoselective
miscellaneous
synthesis
spiro‐hetero/carbocycles.
Advances
decade
made
it
possible
to
synthesize
compounds
with
good
excellent
stereoselectivity
under
appropriate
reaction
conditions.
However,
achieving
high
regioselectivity
several
described
remains
a
challenge.
Organocatalysts
transition‐metal‐based
catalysts
play
crucial
role
this
milestone.
Proposed
mechanisms
supporting
evidence
highlighted
Review.
The
progress
is
immense.
expected
that
synthetic
methods
will
soon
be
developed
can
widely
used
spiro‐heterocycles/carbocycles.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(5), С. 2703 - 2713
Опубликована: Фев. 17, 2023
In
this
paper,
a
series
of
novel
carbazolequinones
were
efficiently
obtained
by
B(C6F5)3-catalyzed
[4
+
2]
cyclization
reaction.
This
protocol
not
only
had
simple
operation,
broad
substrate
range,
and
high
atomic
economy,
but
also
low
catalyst
loading
avoided
using
metal
catalysts.
addition,
we
constructed
diverse
new
carbazole-fused
compounds
under
different
reduction
conditions.
The
results
photophysical
characterization
showed
that
the
structure
derivatives
significant
impact
on
fluorescence
properties.
Green Synthesis and Catalysis,
Год журнала:
2022,
Номер
4(2), С. 78 - 88
Опубликована: Дек. 14, 2022
Indanone-containing
compounds
are
very
important
components
of
various
natural
products,
chemical
drugs,
agrochemicals
and
functionalized
material
fields.
1,3-Indanedione
is
a
typical
cyclic
1,3-dicarbonyl
compound
with
three
contiguous
reactive
electrophilic
nucleophilic
sites.
The
easily
prepared
2-arylidene-1,3-indanediones
active
α,β-unsaturated
carbonyl
could
act
as
1,3-dipolarophile,
1,4-dienophile
1-oxa-1,3-diene,
etc.
On
the
other
hand,
homodimer
(bindone)
cyclotrimer
(truxenone)
derived
from
base-catalyzed
self-condensation
1,3-indanedione
also
compounds.
Therefore,
its
derivatives
can
be
employed
key
substrates
in
domino
multicomponent
reactions.
In
this
review,
we
summarized
recent
progress
on
reactions
1,3-indanedione,
especially
our
achievements
synthetic
applications
for
complex
indanone-containing
carbocyclic
heterocyclic
Green Synthesis and Catalysis,
Год журнала:
2021,
Номер
2(4), С. 362 - 366
Опубликована: Авг. 20, 2021
An
uncommon
aza-Diels-Alder
reaction
of
electron-deficient
azoalkenes
and
3-phenacylideneoxindoles
was
successfully
developed
for
convenient
construction
the
heterocyclic
spirooxindoles.
The
azoalkenes,
which
were
in
situ
generated
from
base
dehydrohalogenation
α-halogeno
N-acylhydrazones,
with
3-methyleneoxindoles
afforded
functionalized
spiro[indoline-3,3′-pyridazin]-2-ones
good
yields
high
diastereoselectivity.
Under
same
conditions,
promoted
N-acylhydrazones
3-aryliminoindolin-2-ones
DCM
at
room
temperature
resulted
spiro[indoline-3,3'-[1,2,4]triazin]-2-ones
satisfactory
yields.
New Journal of Chemistry,
Год журнала:
2023,
Номер
47(14), С. 6694 - 6699
Опубликована: Янв. 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.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(15), С. 10422 - 10429
Опубликована: Июль 12, 2022
DABCO-promoted
cyclization
reaction
of
substituted
2-amino-4H-chromen-4-ones
with
2,6-dibenzylidenecyclohexan-1-ones
was
investigated
under
mild
conditions.
This
provided
a
novel
and
efficient
access
to
the
7,8,9,10-tetrahydro-12H-chromeno[2,3-b]quinolin-12-ones
in
good
yields,
exocyclic
double
bond
which
is
predominantly
E-selective.
