Current Organocatalysis,
Год журнала:
2023,
Номер
11(1), С. 33 - 43
Опубликована: Июль 27, 2023
Abstract:
We
easily
synthesized
two
ionic
liquids,
[BMIM][OH]
and
[BPy][OH],
with
high
yield.
found
that
hydrotalcite
clay,
mediated
by
these
is
a
highly
effective
catalyst
for
synthesizing
biologically
active
1,2-dihydroquinazoline
derivatives.
Using
simple
reaction
protocol
easy
product
isolation
steps,
we
successfully
18
different
derivatives
were
able
to
recycle
the
catalysts
up
8
times.
Overall,
use
of
[BPy][OH]
provide
more
efficient
environmentally
friendly
method
quinazolines
compared
traditional
methods
often
require
harsh
conditions
toxic
reagents.
Background:
1,2-Dihydroquinazolines
are
an
important
class
heterocyclic
compounds
diverse
biological
activities,
including
anticancer,
antifungal,
antibacterial
properties.
They
also
exhibit
other
pharmacological
activities
such
as
antihypertensive,
anti-inflammatory,
antiviral
effects.
The
synthesis
1,2-dihydroquinazolines
dates
early
20th
century
when
they
first
Pictet
Huber
in
1911
condensation
anthranilic
acid
aldehydes
or
ketones
presence
strong
acids.
Since
then,
numerous
have
been
developed
their
synthesis,
cyclization
o-aminobenzamides,
o-aminoaryl
ketones,
Lewis
acids
transition
metals.
In
recent
years,
development
new
synthetic
selective
has
great
interest
chemists,
particularly
pharmaceutical
industry.
These
include
microwave
irradiation,
ultrasound,
liquids
green
solvents.
:
area
research,
continue
be
improve
properties
various
applications.
Methods:
yields.
Results:
our
results
insights
into
sustainable
1,
2-dihydroquinazolines.
Conclusion:
summary,
studies
demonstrated
liquid
clay
catalytic
system
could
used
2-dihydroquinazolines
using
aromatic
carbonyl
compounds,
amino
benzophenone
derivatives,
aldehydes.
electron-donating
substituents
phenyl
group
provided
higher
yields
than
electron-withdrawing
groups,
para
position
aldehyde
had
significant
effect
ortho
meta
position.
Our
was
recyclable
eight
runs
without
loss
activity.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(19), С. 12596 - 12607
Опубликована: Сен. 26, 2022
We
present
a
convenient
and
efficient
protocol
to
synthesize
quinolines
quinazolines
in
one
pot
under
mild
conditions.
A
variety
of
substituted
were
synthesized
good
excellent
yields
(up
97%
yield)
from
the
dehydrogenative
cyclizations
2-aminoaryl
alcohols
ketones
catalyzed
by
readily
available
Co(OAc)2·4H2O.
This
cobalt
catalytic
system
also
showed
high
activity
reactions
2-aminobenzyl
with
nitriles,
affording
various
quinazoline
derivatives
95%
yield).
The
offers
an
environmentally
benign
approach
for
synthesis
N-heterocycles
employing
earth-abundant
salt
ligand-free
Catalysis Science & Technology,
Год журнала:
2022,
Номер
12(18), С. 5695 - 5702
Опубликована: Янв. 1, 2022
The
synthesis
of
N-heterocycles
has
been
considered
an
emerging
area
chemical
research
due
to
their
extensive
utilization
in
pharmaceuticals,
materials
science,
and
natural
product
synthesis.
Frontiers in Chemistry,
Год журнала:
2023,
Номер
11
Опубликована: Март 16, 2023
Quinazolines
are
a
class
of
nitrogen-containing
heterocyclic
compounds
with
broad-spectrum
pharmacological
activities.
Transition-metal-catalyzed
reactions
have
emerged
as
reliable
and
indispensable
tools
for
the
synthesis
pharmaceuticals.
These
provide
new
entries
into
pharmaceutical
ingredients
continuously
increasing
complexity,
catalysis
these
metals
has
streamlined
several
marketed
drugs.
The
last
few
decades
witnessed
tremendous
outburst
transition-metal-catalyzed
construction
quinazoline
scaffolds.
In
this
review,
progress
achieved
in
quinazolines
under
transition
metal-catalyzed
conditions
summarized
reports
from
2010
to
date
covered.
This
is
presented
along
mechanistic
insights
each
representative
methodology.
advantages,
limitations,
future
perspectives
through
such
also
discussed.
Abstract
Cross‐coupling
of
nitriles
and
alcohols
offers
an
environmentally
friendly
atom‐economical
method
for
the
synthesis
various
valuable
compounds.
These
compounds
include
α
‐alkylated
‐olefinated
nitriles,
primary
amines,
imines,
N
‐alkylation
amides,
‐heterocycles,
δ
‐hydroxynitriles,
olefins,
etc
.
Herein,
we
have
reviewed
recent
developments
(from
2013–date)
transition‐metal‐catalyzed
cross‐coupling
alcohols.
A
number
transition
metal
complexes
such
as
noble
metals
Ru
Ir,
well
base
Mn,
Fe,
Co,
Ni
are
presented.
Moreover,
different
product
types,
reaction
conditions
mechanisms
discussed
to
understand
catalyst
development.
Abstract
An
expeditious
strategy
has
been
developed
for
the
synthesis
of
diverse
quinolines,
indenoquinolines
and
acridines
using
KO
t
Bu‐mediated
reaction
conditions.
The
designed
process
utilizes
2‐aminoaryl
carbaldehydes/2‐aminoaryl
ketones
methyl/methylene
group
containing
as
readily
available
feedstock.
chemical
transformation
was
affected
at
room
temperature
within
a
short
duration
time
to
obtain
N
‐heterocycles
yields
up
92
%.
established
also
exhibits
considerable
functional
tolerance
with
an
operational
simplicity.
Abstract
Transition‐metal‐catalyzed
acceptorless
dehydrogenative
coupling
(ADC)
has
emerged
as
a
sustainable
synthetic
strategy
for
the
construction
of
N
‐heteroaromatics.
Herein,
series
water‐soluble
amidato
Ru
catalysts
were
designed,
synthesized,
and
utilized
in
selective
synthesis
2‐substituted
benzimidazoles
from
aromatic
diamines
primary
alcohols,
well
quinolines
substituted
2‐aminobenzyl
alcohols
acetophenones
via
ADC
water.
Catalyst
1
d
bearing
strong
electron‐donating
hydroxyl
group
on
ligand
exhibited
best
catalytic
activity.
The
system
demonstrated
remarkable
efficiency
versatility,
allowing
application
over
40
substrates
two
reactions
with
good
to
high
yields.
Based
control
experiments
density
functional
theory
(DFT)
calculations,
plausible
mechanism
was
proposed,
highlighting
significant
role
functionalized
complexes
catalyzing
alcohol
dehydrogenation
an
outer‐sphere
pathway.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(20), С. 3600 - 3606
Опубликована: Июль 27, 2022
Abstract
A
strategy
for
the
synthesis
of
quinazolines
via
elemental
sulfur‐mediated
oxidative
condensation
nitriles
and
2‐(aminomethyl)anilines
was
developed.
The
reaction
carried
out
under
metal‐/solvent‐free
conditions,
tolerates
a
wide
range
functional
groups
to
provide
corresponding
products
in
56%‐91%
yield,
can
be
performed
on
gram‐scale.
UV/Vis
absorption
fluorescence
spectra
several
product
derivatives
were
measured
study
their
photophysical
properties.
magnified
image
Current Organic Chemistry,
Год журнала:
2024,
Номер
28(4), С. 305 - 318
Опубликована: Фев. 1, 2024
Abstract::
This
study
aims
to
develop
a
practical
and
facile
one-pot
synthesis
of
2-
substituted
quinazolines.
Using
commercially
available
structurally
simple
ruthenium(
II)
complex
as
the
catalyst
synthesize
series
quinazoline
derivatives
via
acceptorless
dehydrogenative
coupling.
The
mechanism
this
reaction
was
explored
by
control
DFT
calculation.
protocol
offers
access
diverse
array
(52
examples)
in
moderate
excellent
yields
(29%-98%).
In
summary,
we
have
developed
an
efficient
ruthenium
(II)-catalyzed
ADC
under
air
atmosphere.
only
produces
hydrogen
water
by-products,
serving
sustainable
atom-efficient
synthetic
approach.
