The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 19, 2024
We
developed
a
method
for
allowing
cascade
cyclization
of
2-nitrochalcones
with
pyrazoles,
imidazole,
and
indazole
in
the
presence
CuI
catalyst,
DBU
base,
THF
solvent.
The
conditions
were
tolerant
an
array
useful
functionalities
including
ester,
nitro,
cyano,
halogen
groups.
A
mechanistic
consideration
was
also
provided,
as
H2O2
presumably
byproduct.
Our
appears
to
be
rare
example
directly
prepare
C3-heterocyclic
unprotected
indoles.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(7), С. 4549 - 4559
Опубликована: Март 22, 2024
An
unexpected
cascade
reaction
of
2-nitrochalcones
with
isocyanoacetates
has
been
reported
for
the
efficient
synthesis
indole
carboxylic
esters
and
pyranoindoles.
The
conversion
was
achieved
by
KOH-catalyzed
cyclization
elimination
nitro
group
final
decarbonylation–aromatization.
method
used
to
synthesize
a
series
potentially
biologically
active
derivatives
(49
examples)
in
67–85%
yields
under
transition-metal-free
catalytic
conditions.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(1), С. 770 - 777
Опубликована: Дек. 19, 2023
A
method
for
aromatic
halogenation
using
a
combination
of
elemental
sulfur
(S8)
and
N-halosuccinimide
has
been
developed.
catalytic
quantity
with
N-bromosuccinimide
(NBS)
N-chlorosuccinimide
(NCS)
effectively
halogenated
less-reactive
compounds,
such
as
ester-,
cyano-,
nitro-substituted
anisole
derivatives.
No
reaction
occurred
in
the
absence
S8,
underscoring
its
crucial
role
activity.
This
system
was
also
applicable
to
iodination
1,3-diiodo-5,5-dimethylhydantoin.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(6), С. 1430 - 1435
Опубликована: Янв. 23, 2024
Abstract
A
substrate‐induced
synthesis
of
coumarin‐fused
quinolinones
is
achieved
from
4‐(phenylamino)‐2
H
‐chromen‐2‐ones
using
N
‐alkyl
amines
as
the
solvent
and
a
carbon
source
under
air
conditions
without
any
catalysts
in
one
pot.
This
protocol
highlights
special
roles
which
were
not
only
used
reactants
but
also
an
internal
oxidant
selectively
activated
‐
α
‐C(
sp
3
)−H
bond.
reaction
features
catalyst‐free,
broad
substrate
scopes
(
27
examples
24
examples),
operationally
simple
for
one‐step
synthesis,
recovery
recycling
solvent.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
90(5), С. 1982 - 1995
Опубликована: Янв. 23, 2025
We
report
a
base-promoted,
metal-free
multicomponent
tandem
reaction,
involving
[4
+
1
1]
cycloaddition
process
between
ortho-substituted
nitroarenes,
aldehydes,
and
ammonium
salts.
Modifying
the
substituents
on
nitroaromatic
compounds
effectively
provides
structurally
diverse
2-substituted
4-alkenylquinazolines
with
good
to
excellent
yields
(77%-90%
quinazoline
51
examples)
high
tolerance
for
various
inorganic
salts
(13
examples,
such
as
NH3·H2O,
NH4Cl,
NH4HF2).
A
new
method
constructing
2,4-substituted
selectivity
from
simple
nitrogen
source
was
developed,
reaction
can
be
scaled
up
gram
scale.
Additionally,
this
also
facilitates
preparation
of
organic
molecules
photophysical
properties,
offering
insights
into
further
transformation
quinazolines.
We
reported
an
unprecedented
chalcogen
element
(Se,
S)
insertion
reaction
with
functionalized
aminomaleimide
to
assemble
medium-sized
nitrogen-containing
organic
selenium/sulfur
catalyzed
by
bases.
During
these
[5/6
+
1]
tandem
annulations,
a
variety
of
low-valent
inorganic
chalcogenides
exhibited
excellent
compatibility,
providing
wide
scope
structurally
diverse
1,4-selenazepanes
(17
examples,
60–71%
yields),
1,4-benzothiazepines
(20
74–86%
and
1,4-thiazines
(6
31–68%
yields).
The
characteristics
this
transformation
are
high
atomic
economy,
formation
two
C–Se
or
C–S
bonds
in
one
step,
avoiding
the
use
unstable
toxic
reagents
under
mild
conditions.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 28, 2025
An
efficient
Cs2CO3-promoted
and
copper(I)-catalyzed
double
cyclization
of
ortho-nitrochalcones
with
vinyl
malononitriles
for
the
de
novo
access
to
a
variety
tri-
tetra-substituted
acridones
their
fused
derivatives
value-added
CN
group
has
been
developed
first
time.
This
one-pot
operation
proceeds
through
Michael-cyclization-aromatization,
followed
by
regioselective
ipso-amination
via
nucleophilic
aromatic
substitution
(SNAr)
reaction,
resulting
in
two
C═C
bonds
C-N
bond
acridone
ring
synthesis.
economic
strategy
based
on
100%
carbon
atoms
ensures
successive
formation
rings
operation,
good
high
yields,
wide
range
substrates,
tolerance
functionalities.
In
addition,
were
converted
into
several
acridines,
highlighting
synthetic
versatility
usefulness
prepared
derivatives.
Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(9)
Опубликована: Июль 24, 2023
Abstract
A
facile
and
highly
efficient
metal‐free
approach
has
been
unfolded
for
the
synthesis
of
novel
dihydrothiochromeno[4,3‐
c
]pyrazoles
using
elemental
sulfur
as
a
powerful
sulfurating
reagent.
This
method
includes
sp
2
C−H
functionalization
followed
by
C−NO
group
displacement
an
odourless
source
activated
DABCO
in
DMSO.
Using
developed
synthetic
strategy,
library
29
]pyrazoles,
incorporating
two
pharmacologically
important
scaffolds
synthesized
52–76%
yield
with
broad
substrate
scope.
sensible
mechanistic
proposal
projected
based
on
control
experiments.
Abstract
A
simple
and
rapid
methodology
for
the
synthesis
of
fully
substituted
pyrroles
was
accomplished
by
reaction
microwave‐assisted
from
amines,
4‐hydroxycoumarins,
ketones.
This
protocol
proceeds
via
ketones
Csp
3
−H
oxidation
Michael
addition/
cyclization/
aromatization
four‐component
cascade
affording
pyrrole
in
moderate
to
excellent
yields
only
min.
Simple
conditions,
high
yields,
compatibility
are
advantages
this
protocol.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 29, 2024
A
substrate-induced
cleavage
and
reorganization
cascade
reaction
of
N
-alkyl
anilines
as
a
carbon
source
the
waste
group
into
chromeno[4,3-
b
]quinolin-6-ones.
