RSC Advances,
Journal Year:
2022,
Volume and Issue:
12(23), P. 14502 - 14508
Published: Jan. 1, 2022
Herein,
we
describe
a
simple
and
general
multi-component
synthesis
of
5-arylselanyluracils
by
the
regioselective
C-H
selenation
uracils.
Reactions
uracils
with
arylboronic
acid
Se
powder
in
presence
AgNO3
(10
mol%)
at
120
°C
under
aerobic
conditions
afforded
various
5-arylselanyluracils.
The
source
introduced
selanyl
group
was
prepared
from
commercially
available
reaction
system,
thereby
ensuring
efficient
protocol.
This
represents
first
example
5-arylselanyluracil
system.
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(19), P. 2346 - 2350
Published: May 27, 2024
Comprehensive
Summary
Catalytic
and
green
strategies
for
the
synthesis
of
privileged
scaffolds
are
synthetically
appealing.
We
now
report
a
radical‐polar
crossover
(RPC)‐enabled
three‐component
cyclization
bromodifluoroalkyls
with
enaminones
6‐aminouraciles
via
visible‐light‐induced
domino
cyclization.
The
reaction
exhibited
broad
substrate
scope
(>
40
examples)
including
complex
molecules,
which
highlighted
utility
this
strategy
construction
library
bioactive
analogs.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(11), P. 1714 - 1755
Published: April 12, 2023
Abstract
In
the
last
decade,
free
radicals
have
found
a
wide
application
in
functionalization
of
unsaturated
compounds,
such
as
alkenes,
alkynes,
and
arenes,
via
free‐radical
addition
to
carbon‐carbon
π‐bonds.
these
processes,
intermolecular
attack
on
aromatic
substrates
represents
challenge
due
relatively
high
resistance
π‐system
reactions
comparison
alkene
C=C
bonds.
The
heterocycles
is
especially
interesting
diversity
their
structures
chemical
properties
well
importance
for
medicinal
chemistry,
agrochemistry,
materials
science.
Addition
C‐centered
widely
known
Minisci‐type
well‐reviewed.
this
paper,
we
summarized
main
achievements
less
explored
group
processes:
by
heteroatom‐centered
(O‐,
N‐,
S‐/Se‐,
P‐radicals)
with
emphasis
papers
published
after
2010.
Literature
analysis
revealed
strong
trend
towards
usage
electrochemistry
photoredox‐catalysis
generation
recent
years.
remaining
fundamental
problem
field
lack
experimental
support
proposed
mechanisms
frequent
existence
several
plausible
reaction
pathways.
progress
mechanistic
studies
can
significantly
improve
prediction
optimal
conditions
depending
structure.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(17), P. 11399 - 11413
Published: Aug. 23, 2022
Herein,
we
report
an
efficient
multicomponent
reaction
for
the
synthesis
of
trisubstituted
thiazoles
involving
a
one-pot
C–C,
C–N,
and
C–S
bond-forming
process
from
readily
available
starting
materials.
The
arylglyoxal,
indole,
aryl
thioamides
in
acetic
acid
medium
under
sealed
heating
conditions
provided
3-(2,4-diarylthiazol-5-yl)-1H-indoles
(4)
good
to
excellent
yields.
Using
similar
strategy,
thioamide,
2,5-dihydroxy-1,4-benzoquinone
structurally
interesting
bis-thiazoles
having
dihydroxy-1,4-benzoquinone
linker
(9).
All
products
were
fully
characterized
by
spectroscopic
techniques.
We
also
recorded
single-crystal
X-ray
diffraction
(XRD)
compounds
4b
9a
unambiguous
structure
determination.
Indole-linked
exhibit
prominent
fluorescence
properties.
relative
quantum
yields
all
thiazole-linked
indoles
measured
dimethyl
sulfoxide
(DMSO)
with
respect
quinine
sulfate
0.1
M
H2SO4
as
reference.
scope
this
was
further
explored
preparing
novel
polymers
11a
11b
using
naphthalene/benzene-1,4-bis(carbothioamide)
polymerization.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(11), P. 6623 - 6632
Published: May 11, 2023
Herein,
we
present
a
copper-mediated
C4-benzylation
of
5-aminopyrazoles
with
3-indoleacetic
acids.
Various
benzylated
are
prepared
in
good-to-excellent
yields
under
basic
and
ligand-free
conditions
the
presence
copper
acetate.
Moreover,
this
benzylation
method
is
applicable
to
other
substrates,
including
naphthylamine,
2-aminochromen-4-one,
enamines.
Some
products
exhibit
antiproliferative
activities
against
cancer
cell
lines.
In
addition,
C4-benzylated
cyclized
into
1H-pyrazolo[4',3':6,7]azepino[3,4-b]indoles
aldehydes
via
one-pot
two-step
processes;
notably,
fluorescence
emissions
large
Stokes
shifts.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(11), P. 6847 - 6856
Published: May 9, 2023
Herein,
a
hitherto
unreported
approach
for
the
synthesis
of
pyrazole/isoxazole-fused
naphthyridine
derivatives
by
three-component
domino
reaction
arylglyoxal
monohydrate,
5-amino
pyrazole/isoxazole,
and
indoles
in
acetic
acid
medium
has
been
reported.
In
this
method,
four
bonds
(2
C-C
2
C-N)
form
one-pot
with
concomitant
formation
two
new
pyridine
rings
via
indole
ring
opening
double
cyclization
reactions.
This
methodology
is
also
applicable
gram-scale
synthesis.
The
mechanism
was
studied
isolating
characterizing
intermediates.
Along
complete
characterization
all
products,
structure
product
4o
unambiguously
confirmed
single
crystal
X-ray
diffraction.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(9), P. 6039 - 6057
Published: April 26, 2023
A
series
of
cascade
reactions
that
produce
a
range
functionalized
aromatic
heterocyclic
compounds
with
pyrazole/pyrazoline
cores
have
been
developed.
The
method
relies
on
metal-free
dehydrogenative
process
to
in-situ
benzaldehydes.
produced
benzaldehyde
was
then
allowed
react
some
other
substances,
including
acetophenone,
pyrazole
amine,
and
phenylhydrazine.
intermediate
from
these
substrates
underwent
several
chemical
processes,
electrocyclization,
the
aza-Diels-Alder
reaction,
formation
intramolecular
C-N
bonds.
These
positive
outcomes
would
open
up
possibility
producing
biologically
active
pyrazolo[3,4-b]pyridine
pyrazoline
derivatives
through
variety
possible
reactions.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(23), P. 16621 - 16632
Published: Nov. 15, 2023
An
enantioselective
construction
of
pyrazolo[3,4-b]pyridones
was
achieved
via
N-heterocyclic
carbene-catalyzed
[3
+
3]
annulation
enals
with
5-aminopyrazoles.
This
protocol
not
only
offers
a
highly
efficient
synthetic
approach
for
the
preparation
various
substituted
but
also
provides
an
effective
method
rapid
synthesis
enantiopure
spirooxindone
derivatives.
