The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 16, 2024
A
robust
pyrrolidine-BzOH
salt-catalyzed
one-pot
three-component
reaction
involving
4-unsubstituted
pyrazolones,
aryl/heteroarylaldehydes,
and
aryl
methyl
ketones
is
reported
for
the
first
time.
This
catalytic
process
fortifies
an
efficient
method,
allowing
practical
synthesis
of
a
wide
array
synthetically
useful
1,3-diarylallylidene
pyrazolones
in
good
to
high
yields
exclusively
their
single
geometrical
isomer
forms.
Furthermore,
this
catalyst
facilitates
sequential
double
condensation
under
thermal
conditions,
thereby
enabling
two
consecutive
C═C
bonds
through
displacement
groups.
Moreover,
organocatalytic
technique
achieves
100%
carbon
atom
economy,
marking
significant
step
forward
toward
sustainable
synthesis.
The Chemical Record,
Journal Year:
2023,
Volume and Issue:
23(7)
Published: Jan. 26, 2023
Abstract
Over
the
last
ten
years,
combination
of
organocatalysis
with
transition
metal
(TM)
catalysis
has
become
one
most
important
toolboxes
used
for
synthesizing
optically
pure
compounds
containing
chiral
quaternary
centers,
including
spiro
heterocyclic
molecules.
The
dominant
method
in
enantioselective
synthesis
based
on
synergistic
includes
aminocatalysis
and
NHC
catalysis,
as
already
established
covalent
organocatalytic
strategies.
Another
area
widely
combined
TM
producing
enantiomerically
enriched
is
non‐covalent
dominated
by
phosphoric
acids,
thiourea,
squaramide
derivatives.
This
review
article
aims
to
summarize
methods
constructing
spirocyclic
heterocycles
a
catalysis.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(11), P. 8230 - 8242
Published: May 14, 2024
We
have
devised
a
highly
diastereoselective
formal
[2
+
1]
annulation
reaction
of
arylidene/alkylidine-pyrazolones
with
in
situ-generated
supported
as
well
standard
pyridinium
ylides
to
construct
spirocyclopropanyl-pyrazolones.
The
cascade
approach
exhibits
wide
range
functional
group
tolerance,
gram-scale
capability,
and
substrate
versatility.
A
diverse
spirocyclic
cyclopropanes
was
synthesized
extensively
both
mediators,
the
pyridine
reused
subsequent
cycles.
Density
theory
calculations
confirmed
formation
spirocyclopropane
lower
energy
pathway.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(23), P. 6819 - 6849
Published: Jan. 1, 2024
This
review
highlights
recent
advances
in
the
atroposelective
preparation
of
axially
chiral
azole
derivatives,
emphasizing
mechanistic
insights
and
synthetic
applications
development
this
class
five-membered
heterocyclic
frameworks.
ChemistrySelect,
Journal Year:
2025,
Volume and Issue:
10(3)
Published: Jan. 1, 2025
Abstract
The
phosphine‐catalyzed
(3
+
2)
annulation
reaction
of
δ
‐hydroxyl‐substituted
allenylic
alcohols
with
pyrazolinone‐derived
ketimines
has
been
developed,
giving
a
variety
spiro
dihydropyrrole‐dihydropyrazolone
derivatives
in
high
yields
good
diastereoselectivities.
Various
unsaturated
and
diverse
worked
well
under
mild
conditions,
31
examples
were
provided
up
to
97%
yield
>20:1
diastereoselectivity.
scale‐up
further
transformations
the
product
successfully
acheived,
three
derivation
experiments
showed
feasibility
product.
These
results
revealed
that
current
could
be
useful
tool
for
synthesis
derivatives.
In
addition,
we
also
investigated
asymmetric
version
this
ketimines,
86%
ee
chiral
was
obtained
use
bifunctional
phosphine
catalyst.
Polycyclic aromatic compounds,
Journal Year:
2022,
Volume and Issue:
43(10), P. 8933 - 8945
Published: Dec. 20, 2022
New
pyrazolone-based
Schiff
bases
were
synthesized
and
characterized
by
various
spectroscopic
analytical
techniques
such
as
1H-NMR,
FTIR,
UV
−
Vis
spectroscopy
elemental
analysis.
Crystal
structures
of
two
the
Schiff-base
(SB)
compounds
obtained
single-crystal
X-ray
crystallography
(SCXRC).
The
target
from
condensation
4-acetyl-3-methyl-1-phenyl-5-pyrazolone
with
1,2-diaminobenzene
(SB1),
4-methyl-1,2-diaminobenzene
(SB2),
4,5-dimethy-1,2-diaminobenzene
(SB3).
Molecular
docking
modeling
was
used
to
study
interactions
these
molecules
SARS-CoV-2
virus
main
proteases
(PDB
ids:
6LU7
7TLL).
estimated
free
binding
energies
(EFBE)
for
all
three
SBs
better
than
standard
drugs
favipiravir
dexamethasone.
Besides,
order
EFBE
−7.68
(SB3)>
−7.36
(SB1)>
−7.06
kcal.mol−1
(SB2)
−10.42
−10.05
−9.69
7TLL.
SB3
showed
best
both
that
is
discussed
based
on
structure–function
relationship.
