The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 20, 2025
In
this
paper,
the
application
of
α-methyl
secondary
enaminones
in
synthesis
tetrahydrofuropyridines
is
described.
The
key
step
methodology
situ
generation
1-azadiene
from
oxidation
enaminone,
followed
by
a
subsequent
inverse-electron-demand
hetero-Diels–Alder
reaction
proceeded
to
give
desired
product.
Mechanistic
studies
and
density
functional
theory
(DFT)
calculations
revealed
detailed
pathway.
Gram-scale
preparation
experiments
further
transformation
product
demonstrate
potential
applicability
method.
addition,
amide
derivatives
could
be
obtained
employing
β-methyl
as
substrates
under
similar
oxidative
conditions.
present
work
opens
new
window
rarely
reported
enaminones.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(21), С. 14957 - 14964
Опубликована: Окт. 19, 2022
The
Dess-Martin
periodinane
(DMP)
reagent-mediated
reactions
of
tertiary
enaminones
with
potassium
thiocyanate
for
the
synthesis
thiazole-5-carbaldehydes
are
developed.
product
formation
involves
cascade
hydroxyl
thiocyanation
C═C
double
bond,
intramolecular
hydroamination
C≡N
and
thiazole
annulation
by
condensation
on
ketone
carbonyl
site,
representing
novel
reaction
pathways
in
between
salt.
DMP
plays
dual
roles
mediating
free
radical
inducing
unconventional
selective
thiazole-5-carbaldehyde
masking
situ
generated
formyl
group
during
process.
Chemical Communications,
Год журнала:
2022,
Номер
58(97), С. 13483 - 13486
Опубликована: Янв. 1, 2022
A
straightforward
approach
to
synthesise
isocoumarins
via
Rh(III)-catalyzed
C-H/C-C
bond
activation/annulation
cascade
of
enaminones
and
iodonium
ylides
has
been
explored.
The
established
protocol
is
characterized
by
an
exceedingly
simple
reaction
system,
high
regioselectivity
good
functional
group
tolerance.
Moreover,
this
strategy
may
provide
a
new
route
cleavage
the
C(sp2)-C(O)
unstrained
ketones.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(20), С. 3539 - 3543
Опубликована: Авг. 26, 2022
Abstract
A
photoinduced
multicomponent
reaction
of
arylamines,
enaminones
and
difluorobromoacetates
for
the
synthesis
2,3‐difunctionalized
quinolines
is
reported.
This
strategy
features
broad
functional
groups
tolerance
wide
substrate
scopes
that
enables
further
synthetic
applications
obtained
products.
Mechanistic
studies
reveal
intermolecular
[3+3]
cyclization
between
in‐situ
generated
1,3‐vinylimine
ions
arylamines
key
step
in
this
transformation.
magnified
image
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(11), С. 1770 - 1776
Опубликована: Март 21, 2023
Abstract
Rh‐catalyzed
C−H
activation
of
arenes
for
oxidative
annulations
with
alkynes
stands
out
as
a
protocol
polycyclic
scaffolds.
This
perspective
drives
us
to
disclose
herein
rhodium
catalyzed
regioselective
triple
annulation
enaminones
hydroxyl‐alkynoates
via
double
functionalization
naphtho‐pyran
Secondary
coordination
OH
in
alkynoate
dictated
the
regioselectivity.
Initial
lactonization
occurred
chemoselectively
on
enamine
part
carbo
rhodation
followed
by
reductive
elimination.
was
scalable
and
has
shown
high
functionality
tolerance.
KIE
studies
were
done
get
insight
mechanism,
some
downstream
transformations
achieved
show
synthetic
potential
method.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(4), С. 2433 - 2442
Опубликована: Фев. 8, 2023
A
simple
and
concise
method
for
the
synthesis
of
cinnolines
has
been
developed
by
reactions
readily
available
enaminones
aryl
diazonium
tetrafluoroboronates.
The
run
efficiently
to
provide
with
broad
diversity
in
substructure
heating
dimethyl
sulfoxide
without
using
any
catalyst
or
additive.
In
addition,
primary
investigation
anti-inflammatory
activity
these
products
leads
observation
p-chlorobenzoyl
(3f)
p-nitrobenzoyl
(3j)
as
attractive
compounds
vitro.
Synthesis,
Год журнала:
2024,
Номер
56(16), С. 2565 - 2571
Опубликована: Апрель 26, 2024
Abstract
Visible-light
photocatalytic
reactions
between
enaminones
and
thioureas
leading
to
thiazole
products
have
been
achieved.
The
annulation
process
consists
of
tandem
C–S
C–N
bond
formation
by
running
under
air
atmosphere
at
ambient
temperature.
Broad
substrate
tolerance
the
sustainable
protocol
has
verified
practical
synthesis
divergent
thiazoles
with
both
monocyclic
fused
cyclic
structures.
Organic Letters,
Год журнала:
2024,
Номер
26(31), С. 6602 - 6607
Опубликована: Июль 30, 2024
Presented
herein
is
a
novel
synthesis
of
indenone-fused
pyran
derivatives
via
the
cascade
reactions
aryl
enaminones
with
cyclopropenones.
The
formation
products
involves
one-pot
procedure
consisting
C–H
bond
and
enamine
functionalization
along
C–C
cleavage
cyclopropenone
1,3-rearrangement
in
situ-formed
allylic
alcohol
moiety
followed
by
intramolecular
O-nucleophilic
addition
Me2NH
elimination.
To
our
knowledge,
this
first
simultaneous
both
indenone
scaffolds
through
concurrent
unsymmetrical
relay
activation
double
C–C/C–O
formation.
Moreover,
usefulness
method
further
showcased
its
suitability
for
large-scale
synthetic
scenarios
diverse
transformations
products.
Chemical Communications,
Год журнала:
2021,
Номер
57(72), С. 9112 - 9115
Опубликована: Янв. 1, 2021
The
C–N
bond
cyanation
of
tertiary
enaminones
has
been
realized
for
the
stereoselective
synthesis
both
(
E
)-
and
Z
)-β-cyano
enones
under
mild
metal-free
conditions,
providing
highly
practical
approaches
β-cyano
enones.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
87(2), С. 1240 - 1248
Опубликована: Дек. 29, 2021
We
present
here
a
rhodium-catalyzed
oxidative
three-point
double
annulation
of
enaminones
with
propargylic
alcohols
via
C–H
and
C–N
bond
activation
to
access
arylnaphthalene-based
lignan
derivatives.
The
key
step
in
the
reaction
is
regioselective
insertion
alcohol
into
rhoda-cycle,
result
hydroxyl
rhodium
coordination.
Necessary
control
experiments
KIE
studies
were
conducted
determine
mechanism.
