Chameleonic Reactivity of Imidoyl Sulfoxonium Ylides: Access to Functionalized Pyrroles and Dihydro-pyridines
Organic Letters,
Год журнала:
2024,
Номер
26(1), С. 62 - 67
Опубликована: Янв. 3, 2024
We
have
found
a
chameleonic
reactivity
of
imidoyl
sulfoxonium
ylides.
On
the
one
hand,
ylides
react
with
electron-deficient
reagents,
such
as
alkynyl
esters,
to
lead
formation
1,2-dihydro-pyridines.
The
methyl
group
attached
sulfur
atom
acts
methylene
donor.
other
pyridinium
1,4-zwitterionic
thiolates,
which
leads
functionalized
pyrroles.
Both
transformations
feature
mild
reaction
conditions
and
good
functional
tolerance.
Язык: Английский
Formation of Trideuteromethylated Artifacts of Pyrrole-Containing Natural Products
Journal of Natural Products,
Год журнала:
2024,
Номер
87(2), С. 415 - 423
Опубликована: Янв. 31, 2024
Pyrrole-containing
natural
products
form
a
large
group
of
structurally
diverse
compounds
that
occur
in
both
terrestrial
and
marine
organisms.
In
the
present
study
formation
trideuteromethylated
artifacts
pyrrole-containing
was
investigated,
focusing
on
discorhabdins.
Three
deuterated
discorhabdins,
1,
3,
5,
were
identified
to
be
isolation
procedure
caused
by
presence
DMSO-d6
during
NMR
sample
preparation
handling.
additional
semisynthetic
derivatives,
7–9,
made
investigation
mechanism
formation,
which
shown
driven
trideuteromethyl
radicals
water,
methanol,
TFA,
traces
iron
solvent.
Generation
also
confirmed
for
other
classes
metabolites,
namely,
makaluvamines,
tambjamines,
dibromotryptamines,
had
been
dissolved
structure
elucidation
process.
Semisynthetic
discorhabdins
assessed
antiproliferative
activity
against
panel
human
tumor
cell
lines,
14-trideuteromethyldiscorhabdin
L
(3)
averaged
low
micromolar
potency.
Язык: Английский
Copper(I) Iodide Catalyzed [3 + 3] Annulation of Iodonium Ylides with Pyridinium 1,4-Zwitterionic Thiolates for the Synthesis of 1,4-Oxathiin Scaffolds
Organic Letters,
Год журнала:
2023,
Номер
25(26), С. 4830 - 4834
Опубликована: Июнь 26, 2023
The
selective
assembly
of
the
1,4-oxathiin
nucleus
has
been
treated
as
a
powerful
strategy
to
access
this
scaffold
present
in
molecules
with
very
interesting
properties.
In
study,
chameleon-like
reactivity
pyridinium
1,4-zwitterionic
thiolates
is
exploited
assemble
core
through
[3
+
3]
annulation.
optimal
annulation
partner
found
be
iodonium
ylide
cyclic
1,3-diketones.
developed
protocol
allows
synthesis
variety
bicyclic
derivatives
under
mild
conditions
copper(I)
iodide
catalysis.
Access
benzoannulated
1,4-oxathiins
achieved
iodine-mediated
aromatization
initially
obtained
compounds.
Язык: Английский
Assembly of Thiazino[3,4‐a]isoquinoline and Thiazepino[5,4‐a]isoquinoline Frameworks from Isoquinolinium 1,4‐Zwitterionic Thiolates via [5 + 1] and [5 + 2] Cycloaddition Reactions
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 18, 2024
Abstract
Two
cycloaddition
modes
of
isoquinolinium
1,4‐zwitterionic
thiolates
have
been
established.
Upon
choosing
α
‐bromo
ketones
as
the
counterpart,
a
range
isoquinoline‐fused
thiazines
can
be
attained
with
yields
ranging
from
moderate
to
excellent
through
formal
[5+1]
reaction
pathway,
exhibiting
remarkable
substrate
adaptability
and
resilience
diverse
functional
groups.
Additionally,
library
unprecedented
thiazepino[5,4‐
]isoquinolines,
novel
category
seven‐membered
heterocycles,
has
synthesized
via
[5+2]
pathway
utilizing
acetylenedicarboxylate
reactive
component.
Notably,
this
process
stands
out
for
its
exceptional
100
%
atomic
utilization
efficiency.
Язык: Английский
Diastereoselective dearomative bifunctionalization of isoquinolinium salts to access bridged tetrahydroisoquinolines
Jiaqi Pei,
Tiantian Tang,
Jianing Zhang
и другие.
New Journal of Chemistry,
Год журнала:
2024,
Номер
48(37), С. 16151 - 16154
Опубликована: Янв. 1, 2024
We
report
a
diastereoselective
dearomative
bifunctionalization
strategy
of
using
isoquinolinium
salts
to
access
bridged
tetrahydroisoquinolines
through
one-pot
three-component
cascade
process.
Язык: Английский
[(5 + 1) ‐ 1] Cyclization of Nitroepoxides to Pyridinium 1,4‐Zwitterionic Thiolates for the Synthesis of Indolizine Derivatives
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 18, 2024
Abstract
The
synthesis
of
indolizine
derivatives
was
achieved
through
the
reaction
pyridinium
1,4‐zwitterionic
thiolates
with
a
diverse
array
2‐methyl‐2‐nitro‐3‐aryloxiranes.
Subsequent
investigations
unveiled
synthetic
route
to
indolizines
via
stepwise
[(5+1)−1]
pathway,
unstable
pyridothiazines
serving
as
transient
intermediates.
DFT
calculations
elucidated
that
this
transformation
entails
sequential
annulation,
deacylation,
desulfurization,
and
oxidation
steps.
Язык: Английский