Oxone® Mediated Regioselective C(sp2)−H Selenylation and Thiocyanation of Pyrazolo[1,5‐a]pyrimidines at Room Temperature
ChemistrySelect,
Год журнала:
2024,
Номер
9(1)
Опубликована: Янв. 2, 2024
Abstract
A
mild
Oxone®
mediated
reaction
for
direct
regioselective
C−H
selenylation
and
thiocyanation
of
pyrazolo[1,5‐
a
]pyrimidines
is
established
at
ambient
temperature.
This
practical
efficient
methodology
employs
as
user
friendly,
green,
non‐toxic
cheap
reagent
to
facilitate
room
The
present
method
offers
high
regioselectivity,
broad
substrate
scope,
conditions
excellent
yields.
Further,
this
eco‐friendly
approach
could
easily
be
extended
other
heterocycles.
Mechanistic
studies
indicate
that
the
occurs
through
electrophilic
substitution
mechanism
via
generation
an
chalcogen
species.
Язык: Английский
I2-Catalyzed Cascade Annulation/Cross-Dehydrogenative Coupling: Excellent Platform to Access 3-Sulfenyl Pyrazolo[1,5-a]pyrimidines with Potent Antibacterial Activity against Pseudomonas aeruginosa and Staphylococcus aureus
ACS Applied Bio Materials,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 19, 2025
The
increasing
resistance
of
bacteria
to
antibiotics
has
become
a
serious
threat
existing
options
for
treating
bacterial
infections.
We
have
developed
synthetic
methodology
3-sulfenyl
pyrazolo[1,5-a]pyrimidines
with
potent
antibacterial
activity.
This
iodine-catalyzed
strategy
been
by
employing
amino
pyrazoles,
enaminones/chalcones,
and
thiophenols
through
intermolecular
cyclization
subsequent
cross-dehydrogenative
sulfenylation.
highly
regioselective
practicable
protocol
utilized
synthesize
structurally
diverse
wide
functionalities.
is
also
extendable
toward
the
synthesis
bis(pyrazolo[1,5-a]pyrimidin-3-yl)sulfanes
from
pyrazole,
enaminones/chalcone,
KSCN
pyrazolo[1,5-a]pyrimidine
direct
acetophenone.
Mechanistic
investigation
disclosed
radical
pathway
C-H
sulfenylation
involvement
3-iodo
as
active
intermediate.
biological
activity
sulfenyl
against
Pseudomonas
aeruginosa
Staphylococcus
aureus,
whereas
sulfinyl
no
such
Sulfenyl
mechanistically
inhibited
growth
accumulation
ROS
well
induction
in
lipid
peroxidation.
Subsequently,
circumstances
changed
membrane
potential
facilitated
interaction
membrane-associated
proteins,
leading
loss
integrity
damage
cell
membranes.
Moreover,
these
derivatives
potentiated
efficacy
commercial
antibiotic
ciprofloxacin
selected
strains
can
be
considered
an
alternative
therapy
Язык: Английский
Exploration of Solvent‐Controlled Reactive Intermediates in the Synthesis of Aryloselenazoles: Altered Chalcogen Bonding Interactions
Chemistry - An Asian Journal,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 29, 2025
Abstract
A
solvent‐controlled
synthesis
process
has
been
developed
for
the
preparation
of
a
wide
spectrum
functional
2‐aryl‐aryloselenazoles.
Investigation
on
reactive
intermediates
through
theoretical
studies
helped
establish
possible
mechanism
present
approach.
Interestingly,
current
strategy
allows
star‐shaped
benzoselenazoles,
which
are
generally
synthesized
following
multistep
processes.
Careful
choice
starting
substrates
led
to
organoselenium
variants
some
metal‐coordinating
ligands
having
structural
similarities
with
several
known
in
area
coordination
chemistry.
The
approach
was
explored
further
gram‐scale
2‐phenyl‐benzoselenazole.
Moreover,
impact
aspects
particularly
remote
functionalization
altering
chalcogen
bonding
interactions
(CBIs)
at
molecular
level
solid‐state
demonstrated.
This
established
by
studying
crystal
structures
few
Язык: Английский
Electrochemical Regioselective C(sp2)-H Bond Chalcogenation of Pyrazolo[1,5-a]pyrimidines via Radical Cross Coupling at Room Temperature
Опубликована: Апрель 9, 2024
In
this
report,
we
disclose
an
electrochemical
approach
for
the
C(sp2)-H
chalcogenation
of
pyrazolo[1,5-a]pyrimidines
at
room
temperature
via
radical
cross-coupling
reaction.
The
reaction
takes
place
within
undivided
cell
employing
graphite
electrodes,
with
TBABF4
acting
as
supporting
electrolyte.
This
technique
offers
a
rapid,
oxidant-free,
and
environmentally
conscious
protocol
achieving
regioselective
specifically
C3
position
pyrazolo[1,5-a]pyrimidines.
Furthermore,
procedure
uses
only
0.5
equivalents
diaryl
chalcogenides
which
underscores
atom
economy
protocol.
Key
attributes
methodology
include
mild
conditions,
short
time,
utilization
cost-effective
electrode
materials,
reliable
achievement
yields
ranging
from
good
to
excellent
friendly
conditions.
Cyclic
voltammetry
studies
quenching
experiments
suggest
pathway
mechanism.
Язык: Английский
Synthesis of organoselenium compounds using electrochemical and photochemical methods as novel approaches in organic chemistry
Tetrahedron,
Год журнала:
2023,
Номер
148, С. 133667 - 133667
Опубликована: Сен. 26, 2023
Язык: Английский
Electrochemical Regioselective C(sp2)–H Bond Chalcogenation of Pyrazolo[1,5-a]pyrimidines via Radical Cross-Coupling at Room Temperature
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(19), С. 14496 - 14504
Опубликована: Сен. 16, 2024
Herein,
we
disclose
an
electrochemical
approach
for
the
C(sp
Язык: Английский