Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(13), P. 2328 - 2332
Published: March 27, 2023
Zinc(II)-catalyzed
[2+2+1]
annulation
of
internal
alkenes,
diazooxindoles,
and
isocyanates
was
successfully
developed
for
the
construction
multisubstituted
spirooxindoles.
This
multicomponent
transformation
involves
in
situ
generation
a
sulfur-containing
spirocyclic
intermediate
from
[4+1]
diazooxindole
to
sulfonyl
isocyanate,
which
subsequently
reacts
as
1,3-dipole
with
alkene,
that
is,
α-oxo
ketene
dithioacetal,
furnish
formal
one-pot
manner.
synthetic
protocol
features
low-toxicity
main
group
metal
catalyst,
readily
available
reagents,
≤96%
yields,
offering
an
efficient
route
spirooxindole
derivatives.
Molecules,
Journal Year:
2023,
Volume and Issue:
28(2), P. 618 - 618
Published: Jan. 7, 2023
Spirooxindoles
occupy
an
important
place
in
heterocyclic
chemistry.
Many
natural
spirooxindole-containing
compounds
have
been
identified
as
bio-promising
agents.
Synthetic
analogs
also
synthesized
utilizing
different
pathways.
The
present
article
summarizes
the
recent
development
of
both
and
synthetic
prepared
from
isatin
or
its
derivatives
reported
last
five
years.
spirooxindoles
are
categorized
based
on
their
mentioned
biological
properties.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(29), P. 5651 - 5693
Published: Jan. 1, 2022
Recent
advances
in
the
chemistry
of
base-,
metal-,
nano-metal
and
organo-catalyst
mediated
achiral
chiral
versions
structurally
diverse
pharmaceutically
relevant
spirooxindoles
are
gently
reviewed.
Applied Organometallic Chemistry,
Journal Year:
2024,
Volume and Issue:
38(4)
Published: Feb. 7, 2024
A
highly
efficient,
green,
and
multicomponent
reaction
method
has
been
developed
for
the
diversity‐oriented
synthesis
of
32
spirooxindole
derivatives
via
formation
cascade
C–N,
C–O,
C–S
bonds.
The
involved
starch‐capped
zinc
oxide
nanocomposite
as
an
effective
heterogeneous
catalyst
with
synergistic
application
ultrasound
on‐water
synthesis.
By
employing
this
approach,
all
desired
products
were
successfully
obtained
high
yields
comparatively
short
times.
Furthermore,
employed
in
process
exhibited
excellent
recyclability,
allowing
its
recovery
reuse
up
to
eight
consecutive
runs
without
any
loss
catalytic
activity.
greenness
protocol
was
evaluated
by
various
green
metrics
such
E‐factor
eco‐score,
result
showed
acceptability
present
organic
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(24), P. 5115 - 5119
Published: June 11, 2024
An
ammonium
ylide-based
relay
annulation
was
disclosed,
which
uses
DABCO
as
the
catalyst
and
oxindole-derived
α,β-unsaturated
ketimines
γ-bromo-crotonates
starting
materials.
This
method
enables
rapid
assembly
of
a
series
structurally
novel
spiro-polycyclic
oxindoles
containing
bicyclo[4.1.0]heptane
moiety
through
simultaneous
generation
three
new
bonds
two
rings
in
one
step
under
mild
reaction
conditions.
Frontiers in Plant Science,
Journal Year:
2023,
Volume and Issue:
14
Published: Feb. 3, 2023
Spirooxindole
alkaloids
feature
a
unique
scaffold
of
an
oxindole
ring
sharing
atom
with
heterocyclic
moiety.
These
compounds
display
extensive
range
biological
activities
such
as
anticancer,
antibiotics,
and
anti-hypertension.
Despite
their
structural
functional
significance,
the
establishment
rationale
spirooxindole
biosynthesis
are
yet
to
be
elucidated.
Herein,
we
report
discovery
characterization
cytochrome
P450
enzyme
from
kratom
(Mitragyna
speciosa)
responsible
for
formation
3-epi-corynoxeine
(3R,
7R)
isocorynoxeine
(3S,
7S)
corynanthe-type
(3R)-secoyohimbane
precursors.
Expression
newly
discovered
in
Saccharomyces
cerevisiae
yeast
allows
efficient
vivo
vitro
production
spirooxindoles.
This
highlights
versatility
plant
enzymes
building
unusual
alkaloid
scaffolds
opens
gateway
access
prestigious
pharmacophore
its
derivatives.
ACS Applied Materials & Interfaces,
Journal Year:
2023,
Volume and Issue:
15(43), P. 50344 - 50359
Published: Oct. 20, 2023
This
study
aims
to
prepare
natural
biomass-based
nonionic
antimicrobial
polymers
with
excellent
biocompatibility,
nonleachability,
activity,
and
polymer
miscibility.
Two
new
cellulose-based
(MIPA
MICA)
containing
many
terminal
indole
groups
were
synthesized
using
a
sustainable
one-pot
method.
The
structures
properties
of
the
characterized
nuclear
magnetic
resonance
hydrogen
spectroscopy
(1H
NMR),
infrared
(FTIR),
wide-angle
X-ray
diffractometry
(XRD),
thermogravimetric
analysis
(TGA),
differential
scanning
calorimetry
(DSC),
electron
microscopy
(SEM),
gel
chromatography
(GPC),
other
analytical
techniques.
results
showed
that
microcrystalline
cellulose
(MCC)
molecules
combined
derivatives
through
an
esterification
reaction
produce
MICA
MIPA.
crystallinity
prepared
MIPA
decreased
after
MCC
modification;
their
morphological
structure
changed
from
short
fibrous
granular
better
thermal
stability
solubility.
paper
diffusion
method
both
had
good
bactericidal
effects
against
two
common
pathogenic
bacteria
Escherichia
coli
(E.
coli,
inhibition
zone
diameters
>22
mm)
Staphylococcus
aureus
(S.
aureus,
>38
mm).
Moreover,
miscibility
biodegradable
poly(vinyl
alcohol)
(PVA),
miscible
composite
films
(PVA-MICA
PVA-MIPA)
phase
compatibility,
light
transmission,
(maximum
decomposition
temperature
>300
°C),
biological
cell
activity
(no
cytotoxicity),
mechanical
fracture
elongation
at
>390%).
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(5), P. 3184 - 3194
Published: Feb. 8, 2022
A
type
of
Morita-Baylis-Hillman
(MBH)
carbonates
has
been
developed
from
ninhydrin.
These
MBH
have
successfully
employed
as
3C-synthons
in
the
organocatalytic
asymmetric
[3
+
2]-annulations
isatin-derived
electron-deficient
olefins,
affording
structurally
diverse
spirooxindoles
high
yield
with
excellent
stereoselectivity.
In
particular,
regioselectivity
was
controlled
by
reaction
partner,
3-methyleneoxindoles
carbonyl
groups
(R
=
ArCO),
β-selective
products
and
ester
CO2Me)
furnishing
γ-selective
products.
The
representative
scale-up
reactions
transformation
product
were
examined.
mechanism
expounded
control
experiments.
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(3)
Published: Feb. 3, 2023
Abstract
Spirocyclic
compounds,
particularly
spirooxindoles
that
comprise
a
tetrahedral
sp
3
‐hybridized
carbon
atom
at
the
C‐3
position
of
an
orthogonally
shaped
bicyclic
structure
have
recently
received
increasing
attention
in
drug
discovery
and
development,
besides
their
major
potential
natural
products
synthetic
organic
chemistry.
They
are
found
to
be
structural
constituents
many
alkaloids,
key
active
building
blocks
for
construction
various
pharmaceutically
significant
molecules.
On
other
hand,
with
awareness
people
about
protecting
health
living
environment
from
pollution
caused
by
chemical
laboratories
industry,
development
method
provides
alternatives
traditional
one
introducing
economical
sustainable
processes
is
scientifically
technically
demanding
but
challenging.
To
address
these
concerns
inspired
photosynthesis
process,
visible
light‐induced
chemistry
appears
highly
economic,
sustainable,
alternative
approach
synthesis.
The
present
mini‐review
aims
highlight
recent
progress
accomplished
straightforward
accelerated
light
irradiation
period
2015
date.
Besides
reviewing
advantages
achieved
this
field,
we
also
attempt
find
out
drawback,
mechanistic
rationalization,
scopes
future
applications.
