Shaking Up the Friedländer Reaction: Rapid, Scalable Mechanochemical Synthesis of Polyaryl‐substituted Quinolines
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 16, 2024
Abstract
Quinolines
are
ubiquitous
heterocyclic
aromatic
scaffolds,
which
can
be
found
in
many
natural
and
synthetic
products.
They
highly
valued
for
their
pharmacological
electrochemical
properties,
encouraging
the
discovery
of
new
routes
quinoline
synthesis
diversification.
In
particular,
polyaryl‐substituted
quinolines
have
recently
surged
as
useful
substrates
a
wide
variety
applications,
yet
remain
difficult
inefficient.
Herein,
we
report
rapid
novel
mechanochemical
Friedländer
under
basic
conditions
using
ball
milling.
The
optimized
reaction
resulted
moderate
to
excellent
yields
ranging
from
48%
>95%
demonstrated
broad
functional
group
tolerance
at
1
hour
times.
We
further
show
route
photocatalyst
DPQN
2,4−di−OMe
photo‐ligand
PPQN
well
OLED
donor‐acceptor
pCzPPQ,
electron
transport
material
oligoquinoline
TQB
organic
semiconductor
DPA.
A
gram
scale
was
also
achieved
Resonant
Acoustic
Mixing
(RAM),
providing
an
isolated
yield
87%
after
simple
recrystallization
ethanol.
Язык: Английский
Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 23, 2025
Quinolines,
a
significant
part
of
nitrogen-containing
heterocycles,
are
widely
found
in
functional
compounds.
Herin,
photochemical
radical
cyclization
reaction
o-vinylaryl
isocyanides
and
aryldiazonium
tetrafluoroborates,
has
been
reported
to
build
2,4-diaryl
quinolines.
Readily
accessible
aryl
diazonium
salts
were
utilized
as
precursors
at
room
temperature.
This
approach
allowed
good
group
tolerance
substrate
applicability.
Язык: Английский
Development of a Recyclable GO-Metformin-Pd(0) Nanocatalyst for Ecofriendly Synthesis of Quinoline-4(1H)-ones and Flavones via Multicomponent-Carbonylation Reactions
Journal of Organometallic Chemistry,
Год журнала:
2025,
Номер
unknown, С. 123699 - 123699
Опубликована: Май 1, 2025
Язык: Английский
Iron-catalyzed formation of six-membered rings from alkyne
Hui Li,
Sang I. Yi,
Chunling Zeng
и другие.
Green Synthesis and Catalysis,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 1, 2025
Язык: Английский
Fe‐Catalyzed, Solvent‐Controlled, Switchable Routes for the Domino Construction of 2,4‐Disubstituted and 4‐Substituted Quinoline Scaffolds
ChemCatChem,
Год журнала:
2024,
Номер
unknown
Опубликована: Июль 27, 2024
Abstract
In
this
report,
we
unveil
a
highly
efficient
novel
protocol
for
the
domino
synthesis
of
2,4‐disubstituted
and
4‐substituted
quinoline
scaffolds.
The
developed
strategy
involves
earth‐abundant
Fe‐catalyzed,
solvent‐controlled,
switchable
routes
selective
construction
frameworks,
achieved
by
using
either
trifluoroethanol
(TFE)
or
methanol
(MeOH)
as
solvent.
By
employing
TFE
solvent
in
Path
A,
alkyne
itself
serves
dual
synthon
through
Fe‐catalyzed
situ
C(
sp
)–C(
)
bond
cleavage,
enabling
two
important
molecules:
quinolines.
Later,
upon
switching
reaction
medium
from
to
MeOH
Path‐B,
only
quinolines
were
obtained
extensively.
oxidation
was
observed
here
functioned
both
an
environmentally
benign
carbon
source.
Both
these
strategies
utilized
prepare
broad
range
mono‐
di‐substituted
derivatives.
application
section
practical
utility,
scale‐up
studies,
along
with
photophysical
properties
synthesized
moiety
are
also
demonstrated.
Язык: Английский
Lewis Acid Catalyzed [4 + 2] Annulation of Propargylic Alcohols with 2-Vinylanilines
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(22), С. 16007 - 16017
Опубликована: Окт. 31, 2023
An
elegant
Lewis
acid
catalyzed,
protection-free,
and
straightforward
synthetic
strategy
for
the
assembly
of
a
series
sophisticated
polycyclic
quinoline
skeletons
employing
propargylic
alcohols
2-vinylanilines
as
substrates
in
presence
Yb(OTf)3
(10
mol
%)
AgOTf
tetrahydrofuran
has
been
described.
This
annulation
protocol,
which
proceeds
through
sequential
Meyer-Schuster
rearrangement/nucleophilic
substitution/deprotonation
sequence,
provides
versatile,
practical,
atom-economical
approach
accessing
derivatives
moderate-to-good
yields.
Язык: Английский
Progression on Oxidative Decyanation Approaches from Secondary Nitriles to Ketones and α‐Aminonitriles to Amides
Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(11)
Опубликована: Сен. 27, 2023
Abstract
The
functional
group
transformation
associated
with
nitrile
moiety
is
considered
a
diligent
research
topic
in
the
synthetic
community
as
it
building
block
for
several
organic
molecules,
including
ketones
and
amides.
Many
methodologies
have
been
developed
synthesizing
amides,
considering
them
analogues
exciting
biological
properties.
However,
there
are
limited
articles
to
synthesize
these
important
classes
of
compounds
via
oxidative
decyanation
nitriles
α‐aminonitriles.
As
protocols
decyanation,
base‐induced
functionality
oxo
carbanion
formation
an
effective
but
under‐explored
area
research.
In
this
context,
we
wish
present
outline
studies
secondary
α‐aminonitriles
afford
corresponding
amides
since
its
inception.
Язык: Английский