European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 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.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(1), P. 62 - 67
Published: Jan. 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.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(28), P. 5120 - 5125
Published: July 12, 2022
A
copper-catalyzed
decarboxylative
cascade
cyclization
of
propargylic
cyclic
carbonates/carbamates
with
pyridinium
1,4-zwitterionic
thiolates
is
developed.
range
fused
polyheterocyclic
compounds
are
obtained
in
moderate
to
good
yields
excellent
diastereoselectivities.
Of
particular
note
that
four
new
bonds
(two
C-C,
one
C-O/N,
C-S)
and
stereocenters
could
be
efficiently
embedded
into
the
tetracyclic
scaffolds
a
single
step.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(11), P. 2813 - 2829
Published: Jan. 1, 2023
This
review
summarizes
the
recent
advances
in
cyclization
reactions
involving
pyridinium
1,
n
-zwitterions
(
=
4
and
5)
highlights
applications
of
efficient
construction
heterocycles.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(17), P. 4612 - 4618
Published: Jan. 1, 2022
Synthesis
of
aryl-fused
1,4-oxathiepines
from
pyridinium
1,4-zwitterionic
thiolates
with
vinylidene
ortho
-quinone
methides
generated
in
situ
via
a
formal
(3
+
4)
pathway.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(11), P. 7199 - 7207
Published: May 12, 2023
Pyridinium
1,4-zwitterionic
thiolates
were
regarded
as
powerful
and
versatile
building
blocks
to
prepare
nitrogen-
sulfur-containing
heterocycles.
Herein,
we
reported
a
copper-catalyzed
formal
[4
+
1]
annulation
of
pyridinium
diazo
compounds
without
any
additives
access
library
trifunctionalized
indolizines
in
good
yields.
Besides,
isoquinolinium
imidazolium
also
applied
this
reaction.
Of
particular
note
is
that
various
functional
groups
such
-CO2R,
-CO2NR2,
-CF3,
-CN,
-(O)P(OR)2
could
be
easily
introduced
into
cycloaddition
products
by
strategy.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 28, 2025
Herein,
we
disclose
a
novel,
mild,
transition-metal-free
approach
to
synthesizing
diversely
functionalized
isothiocyanates
from
the
corresponding
isocyanide
precursors,
achieving
high
excellent
yields
(up
97%).
The
current
method
sheds
light
on
reactivity
of
pyridinium
1,4-zwitterionic
thiolates
as
an
unprecedented
sulfur
source
strikingly
distinct
their
previously
known
in
ionic
annulation
reactions,
showcasing
innovative
organic
synthesis.
Chemical Communications,
Journal Year:
2022,
Volume and Issue:
59(2), P. 239 - 242
Published: Dec. 1, 2022
Chemoselective
annulations
of
phosphoryl
carbenes
generated
from
diazo(aryl)methyl(diaryl)phosphine
oxides
with
pyridinium
1,4-zwitterionic
thiolates
were
performed
under
microwave
irradiation,
affording
1-diarylphosphoryl-1H-benzo[c]thiopyran
derivatives
via
[3+3]
annulation
and
indolizine
([1+5]-1)
P-Cope
elimination
as
the
key
step.
The
annuloselectivity
was
controlled
by
steric
hindrance
pyridiniums
in
thiolates.
Molecules,
Journal Year:
2023,
Volume and Issue:
28(7), P. 3059 - 3059
Published: March 29, 2023
Heteroarene
1,
n-zwitterions
are
powerful
and
versatile
building
blocks
in
the
construction
of
heterocycles
have
received
increasing
attention
recent
years.
In
particular,
pyridinium
quinolinium
1,4-zwitterions
been
widely
studied
used
a
variety
cyclization
reactions
due
to
their
air
stability,
ease
use,
high
efficiency.
Sulfur-
nitrogen-based
1,4-zwitterions,
types
emerging
heteroatom-containing
synthons,
attracted
much
from
chemists.
These
which
contain
multiple
reaction
sites,
successfully
synthesis
three-
eight-membered
cyclic
compounds
over
last
decade.
this
review,
we
present
exciting
progress
made
field
sulfur-
1,4-zwitterions.
Moreover,
mechanistic
insights,
transition
states,
some
synthetic
applications,
challenges
opportunities
also
discussed.
We
hope
provide
an
overview
for
chemists
who
interested
heterocycle
with
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(33), P. 6105 - 6109
Published: Aug. 16, 2023
Pyridinium
1,4-zwitterionic
thiolates
are
usually
used
to
develop
ionic
annulation
reactions.
However,
radical
reactions
were
rare.
We
developed
a
photoredox
catalyzed
[3
+
2]-annulation
reaction
of
pyridinium
with
alkenes,
disclosed
the
new
reactivity
thiolate,
and
provided
synthetic
method
for
dihydrothiophene.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(40), P. 6032 - 6035
Published: Jan. 1, 2023
A
solvent-dependent
strategy
for
the
selective
synthesis
of
isoquinuclidine-
and
tetrahydroisoquinoline
thiazoline
N
,
S
-heterocycles
from
isoquinolinium
1,4-zwitterionic
thiolates
silylketene
acetals
is
reported.
