2‐Hydroxy‐3‐(Pyrrolidin‐1‐yl)‐Indolines: A Platform for Accessing Decorated Deaminokynurenines Enabled by a Double Tautomeric Control
Asian Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 1, 2025
Abstract
In
this
study
we
introduce
indoline
hemiaminals
as
phenacyl
bromide
surrogates
for
the
synthesis
of
deaminokynurenine
derivatives
through
cyclic‐linear
tautomeric
intermediates.
The
reaction
proceeds
a
tandem
process
involving
ring
opening
hemiaminals,
generating
transient
acyclic
aldehydes
which
are
then
trapped
with
in
situ
generated
enolate
species.
Our
protocol
overcomes
traditional
dilemma
production
polar‐mismatch
1,4‐dicarbonyl
compounds
by
utilizing
highly
electrophilic
linear
aldehyde
and
late‐stage
transposition
carbonyl
moiety.
synthetic
utility
our
transformation
was
demonstrated
follow‐up
transformations,
including
first
total
quinoline‐2,4‐dione
alkaloid.
Язык: Английский
Photocatalyzed cascade hydrogen atom transfer for the construction of α-CF3-1,4-diketones
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 5, 2024
A
TBADT-photocatalyzed
cascade
hydrogen
atom
transfer
procedure
was
established
for
the
synthesis
of
α-CF
3
-1,4-diketones
from
aldehydes
and
2-bromo-3,3,3-trifluoro-1-propenes.
Язык: Английский
Cobalt(II)-Catalyzed Proficient Synthesis of Enaminones from Aryl Alkenes and Amines
Synlett,
Год журнала:
2024,
Номер
unknown
Опубликована: Июль 31, 2024
Abstract
A
simple,
cost-effective,
and
modular
strategy
has
been
developed
to
synthesize
synthetically
pharmaceutically
active
enaminones
by
oxidative
amination
of
aryl
alkenes
with
amines
CHCl3,
using
tert-butyl
hydroperoxide
as
an
oxidant.
We
describe
the
synthesis
from
vinyl
arenes
sterically
hindered
N,N-diisopropylethylamine
(DIPEA)
employing
Earth-abundant
cobalt
salt
a
catalyst
within
very
short
reaction
period
for
first
time.
Furthermore,
nitrogen-
oxygen-containing
heterocyclic
compounds
have
synthesized
these
highly
functionalized
enaminones.
Moreover,
various
control
experiments,
such
radical
trapping
reaction,
along
Hammett
analysis
types
substituents
on
styrene
ring
unraveled
detailed
mechanism
this
pathway.
Язык: Английский
Metal-Free Decarboxylative Cyanomethylation of β-Aryl/Heteroaryl Substituted α,β-Unsaturated Carboxylic Acids to γ-Ketonitriles
Organic Letters,
Год журнала:
2024,
Номер
26(46), С. 10051 - 10055
Опубликована: Ноя. 11, 2024
A
decarboxylative
cyanomethylation
of
β-aryl/heteroaryl
substituted
α,β-unsaturated
carboxylic
acids
has
been
accomplished
via
C(sp
Язык: Английский