Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(15), P. 3316 - 3324
Published: Aug. 6, 2024
Abstract
A
domino
reaction
comprising
four
consecutive
steps
based
on
the
strategy
of
isomerization
allylic
alcohols
was
developed.
This
base‐catalyzed
protocol
provided
an
approach
for
constructing
polysubstituted
quinolines
without
additional
additives.
wide
range
di‐
or
trisubstituted
γ‐
aminoaryl
bearing
alkyl
(hetero)aryl
substituents
were
transformed
to
a
structurally
diverse
quinolines.
The
utility
this
transformation
demonstrated
by
application
in
concise
synthesis
several
quinoline
derivatives,
including
natural
products
and
pharmacological
agents.
Preliminary
mechanistic
experiments
suggest
that
alcohol
proceeds
via
intramolecular
1,3‐hydrogen
shift
whereas
aromatization
dihydroquinoline
intermediate
two
possible
pathways
exist:
acceptorless
dehydrogenation
transfer
hydrogenation.
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(36)
Published: April 17, 2023
Highly
enantiomerically
enriched
dihydrohydroquinolines
were
prepared
in
two
steps
from
quinoline.
Addition
of
aryllithiums
to
quinoline
with
tert-butoxycarbonyl
(Boc)
protection
gave
N-Boc-2-aryl-1,2-dihydroquinolines.
These
treated
n-butyllithium
and
electrophilic
trapping
occurred
exclusively
at
C-4
the
dihydroquinoline,
a
result
supported
by
DFT
studies.
Variable
temperature
NMR
spectroscopy
kinetic
data
for
barrier
rotation
carbonyl
group
(ΔG
Dyes and Pigments,
Journal Year:
2023,
Volume and Issue:
222, P. 111859 - 111859
Published: Dec. 4, 2023
Due
to
the
hydrophilicity
of
furan
ring
and
hydroxyl
group,
hydrophobicity
benzene
cyclohexyl
compounds
are
easy
form
hydrophilic
hydrophobic
amphoteric
vesicles
through
self-assembly.
The
self-assembled
were
designed
facilely
synthesized
using
2-furanboronic
acid
H8-BINOL
by
Suzuki
coupling
reaction,
which
could
serve
as
a
novel
probe
with
high
enantioselectivity
for
D/L-Phe.
In
SEM
TEM
images,
after
adding
L-Phe,
vesicle
structure
derivatives
changed
from
spherical
dendritic
nanotube
structures.
On
contrary,
addition
D-Phe,
only
slightly,
indicating
that
material
had
specific
recognition
L-Phe.
Moreover,
new
fluorescent
probes
unique
rigid
structures
obvious
enantioselective
phenylalanine
in
fluorescence
testes.
methanol
solution,
intensity
R-1
S-1
decreased
significantly
at
368
nm
increased
306
nm,
but
D-Phe
no
effect
on
probes,
indicated
good
guiding
amino
acids
chiral
compounds.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(8), P. 1820 - 1826
Published: Feb. 7, 2024
Abstract
Rh(I)‐catalyzed
C8‐selective
C−H
alkenylation
and
arylation
of
1,2,3,4‐tetrahydroquinolines
with
alkenyl
aryl
carboxylic
acids
under
microwave
assistance
have
been
realized.
Using
[Rh(CO)
2
(acac)]
as
the
catalyst
Piv
O
acid
activator,
undergo
decarbonylative
a
wide
range
acids,
affording
C8‐alkenylated
or
arylated
1,2,3,4‐tetrahydroquinolines.
This
method
enables
synthesis
that
would
otherwise
be
difficult
to
access
by
means
conventional
protocols.
Moreover,
this
catalytic
system
also
works
well
in
acids.
The
activity
strongly
depends
on
choice
N
‐directing
group,
readily
installable
removable
‐(2‐pyrimidyl)
group
being
optimal.
pathway
is
elucidated
mechanistic
experiments.
Chinese Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
44(5), P. 1403 - 1403
Published: Jan. 1, 2024
The
structure
of
chiral
saturated
N-heterocyclic
compounds
widely
exists
in
natural
products,
bioactive
molecules,
and
drug
molecules.Catalytic
asymmetric
hydrogenation
aromatic
N-heterocycles
is
one
the
most
effective
methods
for
construction
these
compounds.However,
due
to
strong
conjugation
stability
nitrogen-containing
heterocyclic
poison
effect
nitrogen
atoms
products
on
metal
catalysts,
development
reactions
lags
far
behind,
there
are
relatively
few
research
reports.Therefore,
how
develop
efficient
catalytic
systems
activate
inert
substrate
precisely
control
stereoselectivity
reaction
key
scientific
issue
relevant
research.In
recent
years,
a
series
organo
catalysts
has
led
significant
progress
shown
broad
prospects
its
applications.Considering
that
structures
properties
different
have
remarkable
influence
reactivity,
selectivity,
generality
target
transformations,
an
overview
categorized
provided
according
types
catalysts.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(15), P. 3316 - 3324
Published: Aug. 6, 2024
Abstract
A
domino
reaction
comprising
four
consecutive
steps
based
on
the
strategy
of
isomerization
allylic
alcohols
was
developed.
This
base‐catalyzed
protocol
provided
an
approach
for
constructing
polysubstituted
quinolines
without
additional
additives.
wide
range
di‐
or
trisubstituted
γ‐
aminoaryl
bearing
alkyl
(hetero)aryl
substituents
were
transformed
to
a
structurally
diverse
quinolines.
The
utility
this
transformation
demonstrated
by
application
in
concise
synthesis
several
quinoline
derivatives,
including
natural
products
and
pharmacological
agents.
Preliminary
mechanistic
experiments
suggest
that
alcohol
proceeds
via
intramolecular
1,3‐hydrogen
shift
whereas
aromatization
dihydroquinoline
intermediate
two
possible
pathways
exist:
acceptorless
dehydrogenation
transfer
hydrogenation.
