The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 19, 2024
A
nickel-catalyzed
three-component
carboamination
of
unactivated
alkenes
with
organoboronic
acids
and
anthranils
has
been
achieved
for
the
expedient
synthesis
δ-aryl
γ-amino
acid
derivatives.
The
8-aminoquinoline
(AQ)
directing
group
is
crucial
success
reaction,
anthranil
serves
as
an
arylnitrene
precursor
in
this
conversion.
This
method
features
mild
reaction
conditions,
good
chemo-
regioselectivity,
a
broad
substrate
scope
functional
tolerance.
Organic Letters,
Год журнала:
2020,
Номер
22(15), С. 5990 - 5994
Опубликована: Июль 17, 2020
The
construction
of
eight-membered
rings
is
a
challenging
issue
due
to
unfavorable
transannular
strain
and
entropic
barriers.
We
report
herein
gold-catalyzed
formal
[4
+
2
2]
cycloaddition
reaction
anthranils
with
allenamides
deliver
oxa-bridged
heterocycles
in
accepted
yields
unique
E/Z
configuration.
Moreover,
the
asymmetric
by
using
chiral
phosphoramidite
gold
catalyst
has
also
been
conducted.
The Journal of Organic Chemistry,
Год журнала:
2020,
Номер
85(15), С. 10222 - 10231
Опубликована: Июль 7, 2020
An
efficient
copper-catalyzed
electrophilic
amination
strategy
has
been
established
for
the
rapid
synthesis
of
N-aryl-2-aminophenones
from
readily
available
arylboronic
acids/esters
and
anthranils.
This
protocol
features
good
functional
group
tolerance,
broad
substrate
scope,
operational
simplicity.
Moreover,
a
tandem
C-H
borylation
C-N
coupling
also
developed
to
transform
simple
arenes
valuable
in
one
pot.
Additionally,
synthetic
potential
this
methodology
is
further
demonstrated
by
various
useful
N-heterocycles
derivatives.
Chemical Communications,
Год журнала:
2021,
Номер
57(58), С. 7164 - 7167
Опубликована: Янв. 1, 2021
An
efficient
synthesis
of
indoloindolones
has
been
developed
via
[4+1]
C–H
amination/annulation
cascade
sulfoxonium
ylides
with
anthranils
using
inexpensive
and
air
stable
[Cp*Co(CO)I2]
catalyst.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(27), С. 5567 - 5586
Опубликована: Янв. 1, 2023
Efficacious
protocols
have
been
established
to
synthesize
a
structurally
privileged
Π-extended
coumarin-fused
pyridone
nucleus
by
activating
the
vinylic
C(sp2)-H
bond
of
coumarin-3-carboxamide
under
influence
inexpensive
Ru(II)-metal.
Here
an
N-methoxy
carboxamide
entity
has
exploited
as
chelating
fragment
manifest
functionalization
with
concomitant
(4
+
2)
annulation
reaction,
resulting
in
heterocyclic
ring-forming
along
sulfoxonium
ylide
and
iodonium
representative
bench-stable
carbene
surrogates.
This
diverse
heterocycle
formation
via
insertion
strategies,
is
further
expanded
activate
ortho-C(sp2)-H
bonds
different
heterocycles
employing
sp2-N
moiety
directing
group
develop
acyl-alkylated/alkenylated
quinazolines,
isoxazoles
highly
fluorescent
pyridone-N-oxides.
Intriguingly,
during
evaluation
versatility
current
protocols,
one-pot
double
C-H
activation
rationalized
presence
ylide,
which
results
biologically
potent
benzimidazole-fused
coumarin-centered
bridge-headed
polycyclic
heteroarenes.
Furthermore,
chemo-selective
late-stage
synthetic
transformation
being
designed
differently
substituted
analogues
switching
nature
reducing
agent.
In
addition,
photophysical
experiment
was
done
on
one
pyridine-N-oxide
compound
(7e)
delightfully
it
exhibited
fluorescence
quenching
activity
selectively
Al3+
ions,
appears
be
unique
feature
our
methodology.
Finally,
upon
correlation
merit
developed
pathways,
mediated
strategy
superior.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(44), С. 8794 - 8812
Опубликована: Янв. 1, 2023
Modern
times
have
witnessed
an
uprise
in
the
synthesis
and
derivatization
of
nitrogen-containing
fused
heterocycles.
Amination
reactions
involving
nitrene
chemistry
always
been
most
convenient
choice
for
incorporation
a
nitrogen
atom
molecule.
The
utilization
open
species
harnesses
harsh
conditions.
Hence,
transition
metal-catalyzed
C-H
amination
using
aminating
agents
attractive
choice.
Electrophilic
are
well
exploited
due
to
their
desirable
reaction
Out
all,
anthranils
paved
way
forward
utility
simultaneously
forming
two
new
functional
groups
(amine
carbonyl).
follows
metal-nitrenoid
pathway.
Often,
has
followed
by
Lewis
acid
or
metal-mediated
intramolecular
cyclization
directly
produce
This
review
broadly
demonstrates
as
agent
reactions.
focus
given
scope,
limitations,
mechanistic
understanding
such
electrophilic
agent,
anthranil,
with
metals.
Presented
herein
is
a
nickel-catalyzed
chemo-
and
regioselective
three-component
tandem
carboamination
cyclization
of
terminal
alkynes
with
organoboronic
acids
anthranils
for
facile
modular
access
to
2,3-substituted
quinolines.
In
this
process,
anthranil
has
dual
roles:
serving
as
an
electrophilic
aminating
reagent
redox
buffer
suppress
the
generation
off-cycle
Ni(0)
complex.
Moreover,
anionic
acetylacetonate
(acac)
ligand
was
found
be
vital
ensure
productive
Ni(I)-Ni(III)-Ni(I)
catalytic
cycle.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(17), С. 12107 - 12118
Опубликована: Авг. 24, 2021
A
nickel-catalyzed
polarity-reversed
hydroamination
of
olefins
has
been
achieved
with
anthranils
as
the
electrophilic
aminating
agents
and
hydrosilane
reductant.
This
protocol
provides
a
facile
access
to
N-alkyl-2-aminobenzophenones
that
are
versatile
intermediates
in
organic
synthesis.
wide
range
compatible
this
transformation,
delivering
desired
amines
useful
excellent
yields
(38
examples,
up
92%
yield).
The
utility
is
exhibited
late-stage
functionalization
drug
molecules
valuable
derivatives
obtained
amination
products.
Chemical Science,
Год журнала:
2022,
Номер
13(7), С. 2105 - 2114
Опубликована: Янв. 1, 2022
A
practical
route
for
the
synthesis
of
valuable
3-aryl
anthranils
from
readily
available
and
simple
arenes
has
been
achieved
through
an
electrophilic
substitution
rearomatization
sequence
by
employing
Tf
2
O
as
effective
activator.
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
363(4), С. 1137 - 1141
Опубликована: Дек. 18, 2020
Abstract
A
copper‐catalyzed
site‐selective
C5‐dicarbonylation
reaction
of
anthranils
has
been
developed
for
synthesis
1,2‐dicarbonyl
compounds
using
methyl
ketone
as
a
commercially
available
carbonylation
reagent.
This
process
represents
the
first
example
to
implement
anthranils,
which
involves
an
oxidative
C
sp
3
‐H/C
2
‐H
cross‐coupling
along
with
thermolytic
N−O
bond
cleavage.
magnified
image
