Synthesis,
Год журнала:
2023,
Номер
55(23), С. 4011 - 4019
Опубликована: Авг. 18, 2023
Abstract
Catalyzed
by
2,3-dichloro-5,6-dicyano-1,4-benzoquinone
(DDQ)/tert-butyl
nitrite
(TBN)/O2,
an
efficient
tandem
oxidative
reaction
of
uracils/thiouracil
with
1,3-diarylpropenes
is
disclosed.
It
undergoes
coupling,
intramolecular
cyclization,
and
dehydro-aromatization
to
provide
multi-substituted
pyrido[2,3-d]pyrimidines/thiopyrido[2,3-d]pyrimidines
in
moderate
excellent
yields.
has
the
advantages
high
atom
economy,
green
terminal
oxidant,
metal-free
conditions.
Abstract
Nitrogen‐containing
heterocycles
such
as
imidazoles,
thiazoles,
and
oxazoles
play
a
significant
role
in
the
fields
of
biological
pharmaceutical
chemistry.
These
compounds
were
widely
used
for
agrochemical,
pesticide,
medicinal,
industrial
applications.
Due
to
wide
spectrum
structural
diversity
well
activity
N
‐heterocycles,
plethora
reports
on
their
synthesis
have
appeared
last
few
decades.
However,
developments
various
bond‐forming
strategies
C−C,
C−N,
C−O,
C−S,
N−N,
C−H
activation,
been
powerful
synthetic
tool
derive
copious
‐heterocycles.
The
most
prominent
fascinating
imidazole,
thiazole,
oxazoles,
benzimidazole
moieties
by
C−C
C−N
coupling
reactions,
multi‐component
cycloaddition
etc.
are
discussed
this
study.
studies
demonstrated
enormous
potential
methods
accelerating
modern
chemical
establishing
molecular
beauty
through
bonding.
aspects
methodologies,
like
optimized
conditions,
substrate
scope,
mechanistic
investigations,
detail.
Molecules,
Год журнала:
2023,
Номер
28(10), С. 4153 - 4153
Опубликована: Май 17, 2023
Recent
advances
in
the
environmentally
benign
synthesis
of
aromatic
N-heterocycles
are
reviewed,
focusing
primarily
on
application
catalytic
methods
and
non-traditional
activation.
This
account
features
two
main
parts:
preparation
single
ring
N-heterocycles,
their
condensed
analogs.
Both
groups
include
compounds
with
one,
more
N-atoms.
Due
to
large
number
protocols,
this
focuses
providing
representative
examples
feature
available
methods.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 27, 2025
N-Iodosuccinimide-promoted
cascade
reactions
of
arylidene
isoxazolones
with
amidines
in
p-xylene
were
accomplished,
affording
5-acylimidazoles
good
to
excellent
yields.
Interestingly,
when
the
performed
by
employing
acetonitrile
as
solvent,
4-acylimidazoles
efficiently
obtained.
Mechanistic
studies
indicate
that
formation
imidazolyl
and
acyl
moieties
may
undergo
a
spiroannulation-ring
opening
aromatization-hydrolysis
reaction
sequence.
Based
on
this
solvent-regulated
tandem
strategy,
powerful
protocol
for
switchable
regiodivergent
synthesis
structurally
diverse
was
successfully
established.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7551 - 7556
Опубликована: Май 15, 2023
Herein,
we
report
facile,
atom-economical
syntheses
of
multisubstituted
2,3-dihydropyrroles
using
flavin–iodine-catalyzed
aerobic
oxidative
multistep
transformations
chalcones
with
β-enamine
ketones
or
1,3-dicarbonyl
compounds
and
amines.
Exploiting
coupled
flavin–iodine
catalysis,
the
reaction,
including
C–C
C–N
bond
formation,
is
promoted
only
by
consumption
O2
(1
atm),
thus
allowing
synthesis
that
generates
green
H2O
as
waste.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(10), С. 2081 - 2085
Опубликована: Янв. 1, 2023
Herein,
we
demonstrate
a
green
atom-economical
synthesis
of
benzimidazoles
via
the
flavin-photocatalysed
aerobic
oxidative
cross-dehydrogenative
coupling
toluenes
and
o-phenylenediamines.
The
proposed
metal-free
reaction
proceeds
in
methanol/H2O
under
visible
light
irradiation
by
consuming
only
molecular
oxygen
from
atmospheric
air
produces
water
as
waste.
Arabian Journal of Chemistry,
Год журнала:
2022,
Номер
16(1), С. 104384 - 104384
Опубликована: Окт. 31, 2022
Alzheimer's
disease
(AD)
is
a
neurodegenerative
disorder
and
cholinesterase
(ChE)
enzymes
are
considered
as
crucial
targets
for
the
treatment
of
AD.
Herein,
series
heteroaryl
substituted
imidazole
derivatives
(5a-5x)
was
prepared
using
amino
acid
catalyzed,
one-pot
facile
synthetic
approach.
In
this
context,
catalytic
potentials
different
acids
were
investigated
15
mol%
glutamic
identified
most
suitable
catalyst
to
obtain
target
products
in
good
yields
up
90
%.
These
structurally
exciting
heterocyclic
hybrids
screened
against
acetylcholinesterase
(AChE)
butyrylcholinesterase
(BChE)
enzymes.
This
displayed
moderate
excellent
inhibitory
potential
AChE
with
IC50
values
>
25
µM
active
compound
3-(4-(1-(3,5-dimethylphenyl)-4,5-diphenyl-1H-imidazol-2-yl)-1-phenyl-1H-pyrazol-3-yl)–2H-chromen-2-one
(5x)
value
25.83
±
0.25
µM.This
attributed
hydrophobicity
major
contributory
factor.
The
potent
BChE
1,3-diphenyl-4-(1,4,5-triphenyl-1H-imidazol-2-yl)-1H-pyrazole
(5a)
0.35
0.02
followed
by
other
compounds
5p,
5
m,
5x,
5b,
5c,
5e
5f
<
10
µM.
SAR
studies
further
revealed
that
coumarinyl
moiety
at
R1
position
imidazolylpyrazole
skeleton
significantly
improved
overall
potential.
However,
simple
phenyl
ring
attached
site
highly
effective
selective
inhibition
over
AChE.
Docking
data
also
demonstrated
interaction
5x
docking
score
7564
atomic
contact
energy
(ACE)
–291.90
kcal/mol
whereas
5a
7096
ACE
–332.95
kcal/mol.
results
altogether
suggest
investigations
core
search
leads
towards
designing
new
anti-cholinesterase
drugs
Synlett,
Год журнала:
2023,
Номер
34(19), С. 2309 - 2314
Опубликована: Июль 31, 2023
Abstract
The
reaction
of
5-aminopyrazoles
with
1,3-diarylpropenes
mediated
by
2,3-dichloro-5,6-dicyano-1,4-benzoquinone,
subsequent
intramolecular
cyclization
and
dehydroaromatization
in
the
presence
Cu(OTf)2/tert-butyl
hydroperoxide,
gave
a
series
pyrazolo[3,4-b]pyridines
moderate
to
excellent
yields.
has
advantages
high
atom
economy,
wide
substrate
scope,
one-pot
procedure.
Nanoscale Advances,
Год журнала:
2023,
Номер
5(22), С. 6177 - 6193
Опубликована: Янв. 1, 2023
An
Fe
3
O
4
supported
bistriazolyl-phenanthroline–Cu(
ii
)
complex
was
developed
by
a
novel,
cheap,
environment-friendly
approach
and
utilized
as
green
Lewis
acid
catalyst
in
the
synthesis
of
imidazoles
via
annulation
reactions.
Abstract
A
novel
organophotocatalytic
process
using
riboflavin
derivatives,
which
allows
aerobic
oxidative
multistep
S–S,
S–N,
and
S–O
bond
formations
of
thiols
amines,
is
presented
herein.
The
reaction
proceeded
under
mild
metal-free
conditions
air
(1
atm)
as
an
environmentally
friendly
oxidant,
yielding
sulfinamides
sulfonamides.
