The
rare
[1,2]-sigmatropic
rearrangement
of
sulfoxonium-iodonium
hybrid
ylides
is
described,
which
enables
the
efficient
sulfoxidation/sulfonylation-alkylation
I(III)/S(VI)
with
1,3-dicarbonyls.
By
slight
modification
reaction
conditions,
controllable
alkylation-hydroxylation
and
dialkylation
were
achieved.
This
strategy
affords
a
diverse
array
α,α-difunctionalized
ketones
in
moderate
to
good
yields,
demonstrating
broad
substrate
scope.
These
findings
provide
an
important
advancement
sulfoxonium
highlight
divergent
reactivity
ylides.
Pharmaceuticals,
Год журнала:
2025,
Номер
18(6), С. 797 - 797
Опубликована: Май 26, 2025
Background/Objectives:
In
this
study,
a
novel
series
of
4-(arylchalcogenyl)methyl)-1H-1,2,3-Triazol-1-yl-menadione
derivatives
were
synthesized
to
explore
their
potential
as
new
antituberculosis
(anti-TB)
agents.
Selenium-containing
compounds
are
known
for
significant
antimycobacterial
activity,
which
motivated
inclusion
in
the
design.
Methods:
The
target
via
copper(I)-catalyzed
azide-alkyne
cycloaddition
(CuAAC)
reaction,
affording
yields
ranging
from
34%
93%.
All
evaluated
vitro
anti-TB
activity
against
Mycobacterium
tuberculosis
H37Rv
(ATCC
27294),
well
drug-resistant
strain
(T113/09).
Results:
Several
selenium-containing
exhibited
promising
activity.
Compounds
9b
and
9g
equipotent
first-line
drug,
one
compound
surpassed
its
Notably,
9a,
9b,
9g,
9h
also
showed
efficacy
INH-
RIF-resistant
Mtb
T113/09.
Conclusions:
triazole-menadione
hybrids
both
sensitive
resistant
strains
highlight
candidates
addressing
antimicrobial
resistance
TB
treatment.
Further
investigations
required
understand
mechanisms
action
assess
vivo
therapeutic
potential..
Organic Letters,
Год журнала:
2019,
Номер
21(24), С. 9965 - 9969
Опубликована: Дек. 4, 2019
An
efficient
rhodium-catalyzed
unprecedented
oxa-[2,3]-sigmatropic
rearrangement
of
sulfur
ylide
derived
from
α-thioesters/ketones
and
diazo
carbonyl
compounds
has
been
accomplished
for
the
synthesis
various
sulfur-tethered
vinylogous
carbonates
in
good
to
excellent
yields.
Important
features
developed
reaction
include
wide
functional
group
tolerance,
chemo-
regioselectivity,
involving
motif.
The
present
also
equally
works
well
with
α-selenoesters
seleno-containing
carbonates.
