Decarboxylative Alkylation of Morita–Baylis–Hillman Acetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-Metal Charge Transfer
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 28, 2025
Carboxylic
acids
are
bench-stable
and
readily
available
chemical
feedstocks
that
function
as
optimal
fundamental
synthetic
platforms
for
the
construction
of
C(sp3)–C(sp3)
bonds
via
decarboxylation
processes.
We
present
a
novel
practical
protocol
decarboxylative
alkylation
Morita–Baylis–Hillman
acetates
with
various
carboxylic
photoinduced
iron-mediated
ligand-to-metal
charge
transfer
(LMCT)
process
under
redox-neutral
conditions.
This
method
exhibits
remarkable
tolerance
to
wide
array
acids,
including
primary,
secondary,
tertiary
obviating
requirement
preactivated
radical
precursors.
The
preliminary
mechanistic
analyses
indicate
pathway
is
involved
in
this
catalytic
transformation.
Язык: Английский
N-Arylpyrazole based Scaffolds: Synthesis and biological applications
Journal of Saudi Chemical Society,
Год журнала:
2024,
Номер
28(3), С. 101861 - 101861
Опубликована: Апрель 24, 2024
N-aryl
pyrazoles
are
important
building
blocks
in
many
biologically
active
compounds,
natural
products,
pharmaceuticals,
and
industries.
It
is
an
moiety
of
various
drugs
exhibits
extensive
biological
activities
viz.,
antibiotic,
anticancer,
antifungal,
anti-inflammatory,
anti-coagulant,
analgesic,
antipyretic,
anti-depressant,
insecticidal,
hyperglycemic
activities.
Various
protocols
have
been
designed
for
the
synthesis
facilitated
by
a
wide
variety
metal-based
catalysts
at
high
or
room
temperature,
metal
free
reactions,
named
multicomponent
those
occurring
under
different
electromagnetic
radiations.
ligands
found
to
promote
Cu-catalyzed
N-arylation
pyrazole
mild
conditions
short
time.
This
review
describes
applications
derivatives
reported
during
2019–2023.
Язык: Английский
A Base-dependent Switch in the Reactivity of Baylis–Hillman Ketones with Hydrazines: Access to N'-Alkyl Benzohydrazides and Fluorescent Dihydropyrazoles
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
MBH
ketones
react
with
hydrazines
in
the
absence
of
a
base
to
afford
fluorescent
dihydropyrazoles,
whereas
addition
Et
3
N
leads
formation
benzohydrazides.
Novel
pyrazole
analogues
could
be
obtained
by
oxidation
dihydropyrazoles.
Язык: Английский
Green Light Triggered Radical Annulation for the Synthesis of Indenone by Metal‐Free Photocatalysis
Xing He,
Jia-Qi Ji,
Meng-Yan Zhao
и другие.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 23, 2024
Abstract
Low‐energy
light,
endowing
with
excellent
characteristics
of
lower
energy,
fewer
side
reactions,
more
abundance
in
solar
light.
The
scenario
has
been
developed
for
the
fabrication
indenone
through
a
low‐energy
green
light
driven
radical
annulation
reaction
between
α‐keto
acids
and
internal
alkynes
using
Rhodamine
6G
as
photocatalyst.
Various
kinds
substrates
are
suitable
this
methodology,
affording
corresponding
indenones
greener
efficient
manner.
Язык: Английский
Antibacterial and Antifungal Pyrazoles Based on Different Construction Strategies
Muneeb Ur Rehman,
Fang He,
Xi Shu
и другие.
European Journal of Medicinal Chemistry,
Год журнала:
2024,
Номер
282, С. 117081 - 117081
Опубликована: Ноя. 20, 2024
Язык: Английский
Chemoselective Intramolecular Morita–Baylis–Hillman Reaction; Acrylamide and Ketone as Sluggish Reacting Partners on a Labile Framework
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(2), С. 1073 - 1082
Опубликована: Янв. 2, 2024
Chemoselectivity
is
an
important
issue
frequently
encountered
while
working
over
labile
precursors.
Carbonyl
compounds
with
a
heteroatom
at
the
β
carbon
are
sensitive
precursors
because
they
prone
to
elimination
under
different
conditions.
Morita-Baylis-Hillman
(MBH)
reaction,
although
widespread
method
for
C-C
bond
formation,
has
its
own
limitations.
Acrylamide
and
ketone
such
limitations
of
MBH
reaction.
Using
them
together
intramolecular
(IMBH)
reaction
on
framework
significant
2-fold
synthetic
challenge.
A
highly
chemoselective
IMBH
been
established
using
1,4-diazabicyclo[2.2.2]octane
(DABCO)
as
promoter.
The
protocol
leads
quick
access
diversely
substituted
functionalized
piperidone
in
high
yields.
Various
substitution
patterns
form
34
successful
examples
have
studied.
diastereoselective
version
tolerance
various
functional
protecting
groups
added
advantages
developed
methodology.
tertiary
position
ketone,
however,
led
complete
reversal
selectivity
gave
only
product.
Control
experiments
toward
better
understanding
pattern,
role
catalyst,
mechanistic
study
carried
out.
As
application
adduct,
one-step
allylic
rearrangement
dihydropyridone
also
demonstrated.
Язык: Английский
Overview of Phenylhydrazine‐Based Organic Transformations
ChemistrySelect,
Год журнала:
2024,
Номер
10(1)
Опубликована: Дек. 30, 2024
Abstract
Phenylhydrazines,
comprised
of
a
phenyl
group
attached
with
hydrazine
unit,
contribute
potentially
to
organic
synthetic
transformations.
Because
the
myriad
applications,
last
decade
has
witnessed
considerable
upsurge
interest
perform
various
reactions
catalyzed/mediated/promoted
by
phenylhydrazines.
Some
these
have
shown
high
regioselectivity
in
short
reaction
time
under
mild
conditions.
The
emergence
innumerable
transformations
utilizing
phenylhydrazine
unleashed
numerous
openings
for
development
diverse
heterocyclic
scaffolds.
Given
importance
this
valuable
chemical
entity,
review
highlights
methodologies
Moreover,
present
article
will
considerably
synthesis
as
well
pharmaceutical
chemistry.
Academically,
be
interesting
and
informative
researchers
attempting
develop
new
routes
structures.
Язык: Английский