The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 25, 2024
An
electrochemical
reductive
bimolecular
cycloaddition
of
2-arylideneindane-1,3-diones
has
been
reported
for
the
synthesis
spirocyclopentanole
indane-1,3-diones
bearing
five
contiguous
stereocenters
with
vicinal
tetrasubstituted
stereocenters,
especially
involving
a
quaternary
carbon
center,
in
moderate
to
good
yields
and
excellent
diastereoselectivities.
The
present
protocol
features
mild
reaction
conditions,
no
external
chemical
redox
reagents,
atom
economy,
gram-scale
synthesis.
In
addition,
mechanistic
investigation
indicates
that
reactions
proceed
through
radical
pathway.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(16), P. 11562 - 11580
Published: July 27, 2023
Diverse
functionalized
dihydrobenzofuran
spiro-indanedione-oxindole
scaffolds
were
conveniently
synthesized
by
base-promoted
cyclization
reaction
of
Morita-Baylis-Hillman
(MBH)
carbonates
isatins
and
2-(o-hydroxybenzylidene)-1,3-indanediones.
The
two
diastereomeric
dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines]
could
be
selectively
using
DABCO
or
DMAP
as
a
base
promoter.
More
importantly,
facilitated
the
annulation
MBH
formates
2-(o-hydroxybenzylidene)-1,3-indanediones
selectively,
resulting
in
spiro[cyclopropa[c]chromene-1,2'-indene]-1',3'-diones
dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines].
Additionally,
similar
with
maleimides
afforded
dispiro[indene-2,5'-benzofuro[2',3':1,5]cyclopenta[1,2-c]pyrrole-4',3″'-indolines]
high
yields
diastereoselectivity.
Green Synthesis and Catalysis,
Journal Year:
2023,
Volume and Issue:
5(1), P. 1 - 13
Published: Aug. 15, 2023
Spirooxindole
is
a
compound
with
unique
framework
and
broad
bioactivities
in
medicine.
In
this
study,
we
have
reviewed
various
approaches
or
methods
synthesizing
spirooxindole
derivatives
focused
on
green
synthesis.
Synthesis
of
spirooxindoles
mainly
carried
out
through
multicomponent
reactions
combined
such
as
the
use
heterogeneous
catalysts
(nano-sized,
magnetic,
metal-complex,
metal-organic
catalysts),
deep
eutectic
solvent,
solvent-free
reactions,
catalyst-free
well
ultrasonic
microwaves
irradiation.
The
method
addition
to
obtaining
high
yields,
it
also
offers
reductions
hazardous
chemicals,
energy
use,
purification
processes,
waste
generation.
As
result,
synthesis
are
more
environmentally
friendly.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(24), P. 17181 - 17196
Published: Nov. 28, 2023
A
convenient
synthetic
protocol
for
regioselective
and
diastereoselective
construction
of
complex
dispiro-indanone-fluorenone-oxindole
motifs
was
developed
by
the
base-promoted
annulation
reaction
bindone
MBH
carbonates
isatins
adjusting
conditions.
DABCO
promoted
in
DCM
at
room
temperature,
affording
dispiro[indene-2,4′-fluorene-1′,3″-indoline]
derivatives
good
yields
with
high
diastereoselectivity.
Triethylamine
two
molecular
1,3-indanediones
esters
ethanol
elevated
temperature
selectively
gave
dispiro[indene-2,4′-fluorene-3′,3″-indolines]
moderate
yields.
However,
triethylamine
excess
refluxing
ethanol,
Z-isomer
as
major
product
E-isomer
minor
product.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(15), P. 3277 - 3282
Published: June 4, 2024
Abstract
Indan‐1,3‐diones
stand
as
versatile
precursors
to
a
plethora
of
complex
molecules
with
wide
applications;
however,
their
direct
cross‐coupling
methodologies
remain
largely
unexplored.
Herein,
we
unveil
an
in
situ
triflation‐tandem
strategy
synthesize
diverse
variety
indenones
and
benzofulvenes
from
indan‐1,3‐diones.
The
successful
synthesis
neolignan
natural
product
the
key
intermediate
Indatraline
(antidepressant)
showcased
synthetic
utility
methodology.
enabled
tuning
electronic
characteristics
benzofulvenes,
modulating
HOMO‐LUMO
gaps.
photophysical
properties
these
were
studied,
experimental
results
compared
predictions
obtained
DFT
studies.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(15), P. 3372 - 3378
Published: May 29, 2024
Abstract
Presented
herein
is
a
switchable
synthesis
of
naphthalenone
spiroindanediones
or
4‐acyl‐1‐naphthols
via
condition‐controlled
divergent
cascade
reactions
aryl
enaminones
with
diazoindanediones.
When
the
reaction
was
carried
out
in
presence
an
oxidative
additive,
spiroindanedione
formed
through
C(
sp
2
)−H
alkylation
followed
by
simultaneous
spiroannulation
and
elimination
dimethylamine.
acid
on
other
hand,
4‐acyl‐1‐naphthol
ring
opening
moiety
attacked
situ
released
In
addition,
are
suitable
for
gram‐scale
applications
compatible
variety
substrates.
Moreover,
naphthol
products
allow
structural
elaborations
hybridization
drug,
thus
further
enhancing
value
this
developed
method.
Chinese Journal of Chemistry,
Journal Year:
2023,
Volume and Issue:
42(4), P. 363 - 369
Published: Oct. 2, 2023
Comprehensive
Summary
Herein,
we
report
a
condition‐controlled
divergent
synthesis
of
spiro
indene‐2,1'‐isoindolinones
and
isochroman‐3,1'‐isoindolinones
through
cobalt‐catalyzed
formal
[4
+
1]
1
spirocyclization
aromatic
amides
with
2‐diazo‐1
H
‐indene‐1,3(2
)‐
dione.
When
the
reaction
is
carried
out
under
air
in
ethyl
acetate,
are
formed
Co(II)‐catalyzed
C—H/N—H
spirocyclization.
run
O
2
CH
3
CN,
on
other
hand,
generated
Baeyer‐Villiger
oxidation
situ
as
cheaper
environmental‐friendly
oxygen
source.
In
general,
these
protocols
have
advantages
such
using
non‐precious
earth‐abundant
metal
catalyst,
no
extra
additive,
high
efficiency
regioselectivity.
A
gram‐scale
removal
directing
group
further
highlight
its
utility.
Chemistry - An Asian Journal,
Journal Year:
2024,
Volume and Issue:
19(20)
Published: July 31, 2024
Synthesis
of
functionalized
1,3-indandiones
containing-cyclopentenones
and
-benzotropones
has
been
achieved
by
the
reaction
1,5-diphenylpenta-1,4-diyn-3-ones
with
1,3-indandiones,
bindone
respectively.
The
developed
method
involves
Michael-anti-Michael
addition
cascade
reactions
under
transition-metal-free
conditions.
This
is
first
report
to
synthesise
diverse
benzotropone
fused
transition
metal-free
conditions
from
bindone.
