The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(18), С. 13339 - 13350
Опубликована: Авг. 31, 2023
We
report
a
metal-
and
photocatalyst-free
C3
α-aminomethylation
of
quinoxalin-2(1H)-ones
with
N-alkyl-N-methylanilines.
The
reaction
proceeds
through
the
formation
photoactivated
electron
donor–acceptor
complex
between
present
method
provides
mild
environmentally
friendly
protocol
that
exhibits
good
atom
economy
excellent
functional
group
tolerance
to
obtain
library
biologically
significant
α-aminomethylated
in
yields.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(6), С. 4415 - 4423
Опубликована: Март 2, 2022
An
efficient
synthesis
of
a
variety
[1,2,3]triazolo-[1,5-a]quinoxalin-4(5H)-ones
via
[3
+
2]
cyclization
reaction
by
photoredox
catalysis
between
quinoxalinones
and
hypervalent
iodine(III)
reagents
is
reported.
A
range
were
tolerated
well.
This
allows
access
to
structurally
diverse
in
moderate
good
yields.
Organic Letters,
Год журнала:
2023,
Номер
25(22), С. 4113 - 4118
Опубликована: Май 30, 2023
A
photoredox-catalyzed
1,2-amidoheteroarylation
of
unactivated
alkenes
with
O-acyl
hydroxylamine
derivatives
and
heterocycles
is
presented.
range
heterocycles,
including
quinoxaline-2(1H)-ones,
azauracils,
chromones,
quinolones,
are
capable
for
this
process,
allowing
the
direct
synthesis
valuable
heteroarylethylamine
derivatives.
Structurally
diverse
reaction
substrates,
drug-based
scaffolds,
were
successfully
applied,
demonstrating
practicality
method.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(7), С. 1020 - 1026
Опубликована: Март 10, 2023
Abstract
An
operationally
simple
aqueous
phase
three‐component
photochemical
strategy
for
the
alkylation
of
quinoxalin‐2(1
H
)‐ones
with
diethyl
α
‐bromomalonate
and
unactivated
alkenes
in
absence
both
photoredox
catalysts
additive
has
been
developed.
This
reaction
is
driven
by
activity
electron
donor‐acceptor
(EDA)
complexes
formed
‐bromomalonate.
Irradiation
visible
light
triggered
single‐electron
transfer
(SET)
from
to
‐bromomalonate,
inducing
formation
corresponding
alkyl
radical
subsequent
tandem
reaction.
It
provides
an
efficient
way
construct
alkylated
quinoxalinones
small
molecules.
magnified
image
Molecules,
Год журнала:
2023,
Номер
28(6), С. 2513 - 2513
Опубликована: Март 9, 2023
The
direct
C-H
multifunctionalization
of
quinoxalin-2(1H)-ones
via
multicomponent
reactions
has
attracted
considerable
interest
due
to
their
diverse
biological
activities
and
chemical
profile.
This
review
will
focus
on
recent
achievements.
It
mainly
covers
reaction
methods
for
the
simultaneous
introduction
C-C
bonds
C-RF/C/O/N/Cl/S/D
into
mechanisms.
Meanwhile,
future
developments
multi-component
are
envisaged,
such
as
construction
C-B/SI/P/F/I/SE
through
reactions;
fused
ring
macrocyclic
compounds;
asymmetric
synthesis;
green
chemistry;
bionic
structures
other
fields.
aim
is
enrich
at
C3
position,
which
have
rich
applications
in
materials
chemistry
pharmaceutical
pharmacology.
New Journal of Chemistry,
Год журнала:
2021,
Номер
45(40), С. 18722 - 18763
Опубликована: Янв. 1, 2021
A
gradual
shift
from
metal-catalyzed
to
metal-free
methods
is
occurring,
as
the
latter
are
more
environmentally
benign.
This
review
discusses
sustainable
protocols
for
construction
of
C–C,
C–N,
C–P,
C–S,
and
C–O
bonds
via
C–H
functionalization
quinoxalin-2(1
H
)-ones.
Organic Letters,
Год журнала:
2021,
Номер
23(5), С. 1643 - 1647
Опубликована: Фев. 15, 2021
Reported
herein
is
the
design
and
synthesis
of
new
O-perhalopyridin-4-yl
hydroxylamines
as
shelf-stable
versatile
amidyl-radical
precursors.
The
novel
amination
reagents
can
be
easily
prepared
via
a
single
synthetic
step
from
inexpensive
commercially
available
starting
materials
using
monoprotected
HONH2
amino
source.
potency
developed
was
well
demonstrated
by
direct
series
quinoxalin-2(1H)-ones
their
analogues
under
photocatalytic
conditions,
even
without
any
additive
photocatalysts.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(10), С. 2728 - 2733
Опубликована: Янв. 1, 2022
A
tetrabutylammonium
decatungstate
(TBADT)-photocatalyzed
direct
coupling
of
inert
alkanes
and
quinoxalin-2(1
H
)-ones
with
2
evolution
was
developed
at
room
temperature.
Green Chemistry,
Год журнала:
2022,
Номер
24(21), С. 8460 - 8465
Опубликована: Янв. 1, 2022
Visible
light-driven,
a
radical-cascade
process
for
thioalkylation
of
quinoxalin-2(1
H
)-one
utilizing
styrene
and
aryl
disulfide
derivatives
has
been
discussed.
Organic Letters,
Год журнала:
2022,
Номер
24(4), С. 1055 - 1059
Опубликована: Янв. 26, 2022
A
copper-catalyzed
δ-regioselective
C(sp3)-H
heteroarylation
of
N-fluorosulfonamides
has
been
developed.
broad
range
heteroarenes
were
well
tolerated
and
reacted
with
various
to
give
the
corresponding
heteroarylated
amides
in
good
yields.
Notably,
all
types
(1°,
2°,
3°)
δ-C(sp3)-H
bonds
could
be
regioselectively
activated
through
1,5-HAT
process.
This
protocol
provides
a
practical
strategy
for
functionalization
via
forging
C(sp3)-C(sp2)
bond.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(10), С. 7233 - 7242
Опубликована: Апрель 26, 2024
A
self-catalyzed,
visible-light-induced,
directly
selective
C3–H
aroylation
of
quinoxalin-2(1H)-ones
via
energy
transfer
and
hydrogen
atom
(HAT)
catalysis
has
been
developed.
The
method
is
highly
atom-economical,
eco-friendly,
easy
to
handle.
Notably,
the
reaction
proceeded
efficiently
with
ambient
air
as
sole
oxidant
at
room
temperature.
