The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 25, 2024
An
electrochemical
reductive
bimolecular
cycloaddition
of
2-arylideneindane-1,3-diones
has
been
reported
for
the
synthesis
spirocyclopentanole
indane-1,3-diones
bearing
five
contiguous
stereocenters
with
vicinal
tetrasubstituted
stereocenters,
especially
involving
a
quaternary
carbon
center,
in
moderate
to
good
yields
and
excellent
diastereoselectivities.
The
present
protocol
features
mild
reaction
conditions,
no
external
chemical
redox
reagents,
atom
economy,
gram-scale
synthesis.
In
addition,
mechanistic
investigation
indicates
that
reactions
proceed
through
radical
pathway.
Organic Letters,
Год журнала:
2023,
Номер
25(5), С. 838 - 842
Опубликована: Янв. 27, 2023
A
copper-catalyzed
annulation
of
O-acyl
oximes
with
cyclic
1,3-diones
has
been
developed
for
the
concise
synthesis
7,8-dihydroindolizin-5(6H)-ones
and
cyclohexanone-fused
furans
through
substituent-controlled
selective
radical
coupling
process.
2-Alkyl
undergo
C-C
coupling,
while
2-unsubstituted
C-O
coupling.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
88(8), С. 5212 - 5219
Опубликована: Окт. 23, 2022
Electroreductive
ring-opening
carboxylation
of
cycloketone
oxime
esters
with
atmospheric
carbon
dioxide
is
reported.
This
reaction
proceeded
under
simple
constant
current
conditions
in
an
undivided
cell
using
glassy
as
the
cathode
and
magnesium
sacrificial
anode,
providing
substituted
γ-
δ-cyanocarboxylic
acids
moderate
to
good
yields.
Electrochemically
generated
cyanoalkyl
radicals
anion
are
proposed
key
intermediates.
An
iron-catalyzed
[3
+
2]
annulation
of
O-acyl
oximes
with
2-hydroxy-1-naphthoates
has
been
developed.
This
strategy
features
the
simultaneous
activation
both
substrates
to
form
two
radical
intermediates.
Subsequent
selective
C-N
coupling
followed
by
sequential
condensation
and
1,3-ester
migration
affords
1H-
or
3H-benzo[g]indoles.
In
terms
derived
from
4-oxocyclohexanone
4-azacyclohexanone,
further
ring-opening
furnishes
2-(2-hydroxyethyl)-
2-(2-aminoethyl)-1H-benzo[g]indoles.
An
iron-catalyzed
double
annulation
of
O-acyl
oximes
with
fumaronitrile
has
been
developed
for
the
concise
synthesis
polysubstituted
4-cyano-7-azaindoles.
This
method
enables
construction
two
fused
heterocycles
in
a
one-step
reaction
using
readily
available
starting
materials
under
redox-neutral
conditions.
Chemical Communications,
Год журнала:
2023,
Номер
59(71), С. 10636 - 10639
Опубликована: Янв. 1, 2023
The
first
copper-catalyzed
three-component
annulation
of
α,β-unsaturated
ketoximes,
1,3-dicarbonyls
and
paraformaldehyde
has
been
documented.
This
novel
strategy
achieved
the
two
C-C
bond
cleavage
1,3-dicarbonyl
compounds
directly
as
a
single-carbon
synthon
provided
new
highly
efficient
method
for
synthesis
2,3-disubstituted
pyrroles
in
moderate
to
good
yields
with
broad
functional
group
compatibility.
Chemical Communications,
Год журнала:
2023,
Номер
59(90), С. 13462 - 13465
Опубликована: Янв. 1, 2023
Herein,
we
introduce
a
photocatalyst-
and
additive-free
method
for
the
preparation
of
valuable
3,3-disubstituted
oxindoles
bearing
trifluoromethyl
alcohol
moieties
from
readily
available
acrylamides
cheap
trifluoropyruvates.
The
excited
trifluoropyruvates
under
ultraviolet-light
irradiation
react
efficiently
with
delivering
variety
broad
functional
group
tolerance
moderate
to
good
yields.
This
protocol
features
mild
reaction
conditions,
simple
operation
ready
scalability.
Green Synthesis and Catalysis,
Год журнала:
2023,
Номер
4(2), С. 150 - 153
Опубликована: Янв. 3, 2023
An
iron-catalyzed
[4
+
2]
annulation
of
amidines
with
α,β-unsaturated
ketoxime
acetates
is
described.
This
strategy
employs
as
CN
units
and
provides
a
new
protocol
for
the
construction
2,4,6-trisubstituted
pyrimidines
under
batch
continuous
flow
conditions
in
moderate
to
good
yields,
exhibiting
functional
group
tolerance,
scalability
operational
simplicity.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(17), С. 12236 - 12243
Опубликована: Авг. 23, 2023
The
copper-catalyzed
[4
+
2]
annulation
of
α,β-unsaturated
ketoximes
with
activated
nitriles
for
the
rapid
construction
2,4,6-trisubstituted
pyrimidines
in
moderate
to
good
yields
has
been
developed.
reaction
features
synthetic
simplicity,
functional
group
tolerance,
and
gram-scale
applicability.
A
plausible
mechanism
is
proposed
based
on
mechanistic
investigations.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(22), С. 3867 - 3873
Опубликована: Окт. 7, 2022
Abstract
Palladium‐catalyzed
coupling
reaction
followed
by
dual
annulation
has
been
achieved
for
the
synthesis
of
various
triazolo/pyrrolo
fused
benzofuro‐quinolines
from
readily
available
starting
materials.
The
developed
protocol
proceeds
through
palladium‐catalyzed
Sonogashira
coupling,
benzannulation
C−H
activation
triggered
second
cascades
in
a
single
pot.
In
particular,
polycyclic
compound
formed
this
method
consists
three
different
heterocyclic
structures:
benzofuran,
quinoline,
and
triazole/pyrrole.
provides
simple
access
to
obtain
range
benzofurotriazalo/pyrrolo‐quinolines
good
moderate
yields.
magnified
image
