Chinese Journal of Chemistry,
Journal Year:
2018,
Volume and Issue:
36(12), P. 1182 - 1186
Published: Oct. 10, 2018
Abstract
A
well‐designed
three‐component
reaction
was
developed
to
construct
a
class
of
optically
active
carbazolespirooxindole‐urazoles
in
good
yields
with
excellent
stereoselectivities
via
tandem
Diels‐Alder
and
ene‐reaction.
The
driving
force
originating
from
aromatization
situ
generated
carbazolespirooxindole
the
high
reactivity
4‐phenyl‐3
H
‐1,2,4‐triazole‐3,5‐dione
facilitate
ene‐reaction
mild
conditions.
Control
experiments
indicated
that
most
likely
came
spatial
configuration
carbazolespirooxindole.
obtained
products
could
be
converted
other
synthetic
useful
structures
diverse
functionalization.
Organic & Biomolecular Chemistry,
Journal Year:
2019,
Volume and Issue:
18(1), P. 163 - 168
Published: Dec. 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,
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.
The Journal of Organic Chemistry,
Journal Year:
2019,
Volume and Issue:
84(19), P. 12437 - 12451
Published: Sept. 9, 2019
The
acetic
acid
catalyzed
three-component
reaction
of
pyrrolidine,
aromatic
aldehydes,
and
3-arylideneoxindolin-2-ones
in
refluxing
toluene
afforded
functionalized
7′-arylidenespiro[indoline-3,1′-pyrrolizines]
good
yields
with
high
diastereoselectivity.
similar
2-arylidene-1,3-indanediones
also
gave
7′-arylidenespiro[indene-2,1′-pyrrolizines]
yields.
However,
the
3-phenacylideneoxindoles
resulted
a
mixture
spiro[indoline-3,1′-pyrrolizines]
7′-arylidene-substituted
spirooxindoles
moderate
mechanism
included
generation
azomethine
ylides,
β-C–H
functionalization
sequential
[3
+
2]
cycloaddition.
obtained
spirooxindole
derivatives
were
investigated
by
vitro
evaluation
against
mouse
colon
cancer
cells
CT26
human
liver
HepG2
MTT
assay.
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.
Green Synthesis and Catalysis,
Journal Year:
2021,
Volume and Issue:
3(1), P. 53 - 58
Published: Oct. 22, 2021
A
new
DBU-catalyzed
formal
[4
+
2]
cycloaddition
between
ortho-hydroxyphenyl-substituted
para-quinone
methides
and
electron-deficient
dienophiles
including
3-methyleneoxindoles
2-aryldeneindene-1,3-diones
was
established.
wide
range
of
functionalized
spiro[chromane-3,3′-indolines]
spiro[chromane-3,2′-indenes]
were
successfully
synthesized
in
good
yields
with
high
diastereoselectivity.
The
features
the
reaction
included
readily
available
substrates,
mild
conditions,
convenient
methodology
functional
group
tolerance.
The Journal of Organic Chemistry,
Journal Year:
2018,
Volume and Issue:
84(2), P. 622 - 635
Published: Dec. 24, 2018
The
multicomponent
reaction
of
l-proline,
isatins,
and
excess
methyl
propiolates
in
methanol
unexpectedly
afforded
2-(oxoindolin-3-ylidene)propylidene)pyrrolidin-1-yl)acrylates
good
yields,
the
products
subsequently
converted
to
unique
nine-membered
pyrrolo[1′,2′:1,9]azonino[6,5,4-cd]indoles
presence
p-TsOH.
Furthermore,
N-benzylisatins,
alkyl
refluxing
chloroform
unprecedentedly
resulted
eight-membered
azocino[1,2-a]benzo[c][1,5]diazocines
as
main
product.
molecular
structures
polyheterocyclic
compounds
were
confirmed
by
determination
19
single
crystal
structures.
mechanism
was
believed
contain
sequential
1,3-dipolar
cycloaddition,
addition
cyclic
tertiary
amine
propiolate,
fascinating
ring
opening
well
rearrangement
process.
N-substituent
on
isatins
played
a
critical
role
different
patterns.
The Journal of Organic Chemistry,
Journal Year:
2018,
Volume and Issue:
83(11), P. 5909 - 5919
Published: April 26, 2018
A
HOTf
catalyzed
three-component
reaction
of
indoles,
acetophenones,
and
(
E)-3-phenacylideneoxindolinones
resulted
in
the
unexpected
polysubstituted
3-(9
H-carbazol-2-yl)indolin-2-ones
good
yields.
similar
with
various
cyclic
ketones
afforded
corresponding
carbocyclic
fused
H-carbazol-2-yl)indolin-2-ones.
On
other
hand,
E)-3-arylideneoxindolinones
gave
expected
spiro[tetrahydrocarbazole-3,3'-oxindoles]
through
a
domino
alkenylation/Diels-Alder
reaction.
The
unusual
different
reactivity
reactions
was
believed
to
involve
paths
caused
by
existence
carbonyl
group.
