RSC Advances,
Journal Year:
2022,
Volume and Issue:
12(54), P. 34941 - 34945
Published: Jan. 1, 2022
The
application
of
2-aryl/heteroarylidene-1H-indene-1,3(2H)-dione
as
an
activated
olefin
source
in
the
DABCO-catalyzed
[3
+
2]
cycloaddition
with
N-2,2,2-trifluoroethylisatin
ketimines
has
been
disclosed.
This
highly
efficient
1,3-dipolar
reaction
offered
a
variety
trifluoro
methyl
group
bearing
spiro-pyrrolidine
linked
oxindoles
four
consecutive
stereocentres
good
to
excellent
yield
and
diastereoselectivity.
synthetic
practicality
protocol
was
established
by
demonstrating
enantioselective
construction
spiro-pyrrolidine-oxindoles
two
vicinal
spiro-quaternary
chiral
centres
enantioselectivity
(>90%
ee)
using
ultralow
loading
quinine
catalyst
at
room
temperature.
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.
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.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(42), P. 7790 - 7795
Published: Oct. 14, 2022
We
have
developed
an
efficient
protocol
for
the
construction
of
polycyclic
dihydrobenzofuran
spirooxindole
scaffolds
via
base
promoted
cascade
annulation
Morita-Baylis-Hillman
(MBH)
carbonates
isatins
with
ortho-hydroxychalcones
or
ortho-hydroxy-β-nitrostyrenes.
The
complex
compounds
were
conveniently
synthesized
in
satisfactory
yields
and
high
diastereoselectivity.
This
provides
a
swift
convenient
approach
assembly
diverse
highly
functionalized
spirooxindoles
also
features
broad
substrate
scope,
molecular
convergence,
excellent
atomic
economy.
RSC Advances,
Journal Year:
2023,
Volume and Issue:
13(11), P. 7063 - 7075
Published: Jan. 1, 2023
Recent
updates
on
the
synthesis
of
CF
3
-containing
spirocyclic-oxindoles
by
employing
N
-2,2,2-trifluoroethylisatin
ketimines
are
described
in
this
review
article.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(7), P. 1518 - 1530
Published: Jan. 1, 2023
A
highly
efficient
pot,
atom,
and
step
economical
method
for
the
construction
of
pharmacologically
potent
structurally
functionalized
1,4-dihydropyridines,
quaternary
centered
C-3
spiro[indoline-3,4'-pyridines],
C-11
spiro[indeno[1,2-b]quinoxaline-11,4'-pyridines]
via
rose
bengal
photoredox
catalysis
under
blue
LED
irradiation
in
an
aqueous
medium
at
room
temperature
has
been
developed.
The
products
were
isolated
excellent
yields
within
a
short
reaction
time
variety
functional
groups
transition
metal-
ligand-free
energy-efficient
conditions
green
solvent
system
with
high
mass
efficiency
process
intensity,
which
are
key
advantages
current
work.
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.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(18), P. 3739 - 3743
Published: April 29, 2024
An
enantioselective
Pd-catalyzed
intramolecular
dearomative
reductive
Heck
reaction
of
N-(o-bromoaryl)
indole-3-carboxamide
is
developed.
By
employing
Pd(dba)2/SPINOL-based
phosphoramidite
as
the
chiral
catalyst
and
HCO2Na
hydride
source,
a
series
enantioenriched
spiro
indolines
bearing
vicinal
stereocenters
were
afforded
in
moderate
to
good
yields
with
excellent
enantioselectivities.
The
formal
tetrasubstituted
alkene
β-hydrogens
therefore
realized
by
inhibiting
β-H
elimination.
