3‐Alkenylation of Oxindoles, Benzofuranones and Indoles from Linear Propanols
ChemistrySelect,
Год журнала:
2025,
Номер
10(13)
Опубликована: Март 30, 2025
Abstract
A
novel
organocatalytic
one‐pot
cascade
alcohol
oxidation
iminium
activation
strategy
for
the
3‐alkenylation
of
oxindoles,
benzofuranones,
and
indoles
from
substituted
propanols
with
excellent
stereo‐selectivity(E/Z
up
to
>99:1)
has
been
developed.
This
seven‐step
process
involves
α
‐spirocyclopropanation
benzofuran‐2‐ones,
indolin‐2‐ones,
indoles,
by
adjusting
reaction
temperature
base
feeding,
stable
‐spirocyclopropyl
propionaldehyde
intermediate
was
isolated.
Язык: Английский
DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons
Organic Letters,
Год журнала:
2024,
Номер
26(43), С. 9322 - 9327
Опубликована: Окт. 24, 2024
The
present
work
develops
a
DMAP-catalyzed
[3
+
2]
cycloaddition
of
vinyl
oxiranes
with
activated
ketone
compounds,
affording
dioxolane
derivatives
moderate
to
excellent
yields.
This
approach
represents
the
first
Lewis
base
(LB)-catalyzed
ring-opening
reaction
epoxides,
simultaneously
providing
rare
oxygen-containing
active
intermediate
in
this
field.
gram-scale
preparation
and
facile
derivatization
cycloadduct
highlight
significant
synthetic
potential
strategy.
Язык: Английский
Et3N-catalyzed [3 + 2] annulation reaction of β-oxo-acrylamides with diethyl 2-oxomalonates: facile access to oxazolidin-4-one derivatives
Chemistry Letters,
Год журнала:
2024,
Номер
53(7)
Опубликована: Июль 1, 2024
Abstract
A
new
and
effective
method
for
the
[3
+
2]
annulation
of
β-oxo-acrylamides
with
diethyl
2-oxomalonate,
catalyzed
by
NEt3,
has
been
developed
to
be
carried
out
under
mild
reaction
conditions.
This
approach
offers
a
direct
route
synthesize
oxazolidin-4-one
derivatives
yields
ranging
from
58%
76%.
The
process
is
notable
being
highly
atom-efficient
operationally
simple.
Язык: Английский
Regiospecific Synthesis of Thioether‐Linked 3‐Hydroxy Oxindoles From Spiroepoxy Oxindoles and Their Cytotoxicity Evaluation
ChemistrySelect,
Год журнала:
2024,
Номер
9(46)
Опубликована: Дек. 1, 2024
Abstract
A
facile
synthesis
of
thioether‐linked
3‐hydroxy
oxindoles
was
achieved
through
regiospecific
ring‐opening
spiroepoxy
with
oxadiazole‐2‐thiols
and
benzimidazole‐2‐thiols
as
nucleophiles.
The
thiol
heteronucleophile
attacks
from
the
less
hindered
position
spiroepoxides,
yielding
3‐substituted‐3‐hydroxy
in
high
yields
(up
to
86%).
synthetic
procedure
offers
an
attractive
route
for
diversely
substituted
that
are
prominent
frameworks
many
natural
products.
Further,
vitro
cytotoxicity
evaluation
shows
most
these
molecules
possessed
considerable
cytotoxic
activity
against
a
panel
human
cancer
cell
lines
by
comparing
5‐fluorouracil
(5‐FU)
control.
morphological
studies
like
phase
contrast,
AO/EB,
DAPI
potent
compound
5e
highlight
apoptotic
features
on
skin
melanoma
(SKMEL‐29).
Additionally,
also
studied
inhibition
tubulin
polymerization,
result
correlated
molecular
docking
studies.
Язык: Английский