Herein,
visible-light-induced
annulation
of
benzothioamides
with
sulfoxonium
ylides
to
furnish
thiazole
derivatives
is
developed
under
transition-metal-,
photocatalyst-,
and
oxidant-free
conditions.
This
protocol
exhibits
good
substrate
scope,
affording
the
desired
products
satisfied
yields
in
a
mild
green
manner.
Detailed
mechanistic
studies
suggest
that
benzothioamide
plays
dual
role
this
reaction.
Under
visible-light
irradiation,
excited
benzothioamide,
its
triplet
state,
could
undergo
S
attack
C═S
moiety
ylide
followed
by
dissociation
dimethyl
sulfoxide
H
migration
give
key
adduct.
In
addition,
act
as
an
organocatalyst
facilitate
intramolecular
cyclization
adduct
proton
transfer
steps.
After
dehydration
cyclized
intermediate,
can
be
produced.
Green Chemistry,
Год журнала:
2023,
Номер
25(14), С. 5539 - 5542
Опубликована: Янв. 1, 2023
With
formaldehyde
as
an
atom-economical
carbonyl
synthon,
the
EtOH-catalyzed
electrochemical
multicomponent
synthesis
of
various
imidazolidine-fused
sulfamidates
under
organic
oxidant-free,
energy-saving
and
mild
conditions
was
developed.
Organic Letters,
Год журнала:
2024,
Номер
26(25), С. 5263 - 5268
Опубликована: Июнь 14, 2024
A
green
and
sustainable
electrochemical
oxidative
cyclization
of
enaminones
with
thioamides
under
metal-
oxidant-free
conditions
has
been
developed,
providing
an
efficient
approach
for
thiazole
synthesis.
Furthermore,
1,2,4-thiadiazoles
can
be
selectively
accessed
via
the
dimerization
in
absence
enaminones.
Organic Letters,
Год журнала:
2023,
Номер
25(12), С. 2139 - 2144
Опубликована: Март 22, 2023
The
three-component
reactions
of
enaminones,
α-diazo
esters/ketones,
and
t-butyl
nitrite
(TBN)
for
the
switchable
synthesis
isomeric
isoxazoles
have
been
realized.
catalysis
with
Cu(II)
salt
provides
3,4-disubsituted
via
[3
+
2]
cycloaddition.
On
other
hand,
Ag(I)
identical
substrates
leads
to
reversed
C3
C4
substitution
based
on
a
key
[2
1]
Chemical Communications,
Год журнала:
2023,
Номер
59(27), С. 4036 - 4039
Опубликована: Янв. 1, 2023
The
synthesis
of
N-naphthyl
pyrazoles
has
been
realized
by
the
direct
three-component
reactions
enaminones,
aryl
hydrazine
hydrochlorides
and
internal
alkynes
via
Rh(III)
catalysis.
synthetic
employing
simple
substrates
lead
to
simultaneous
construction
dual
cyclic
moieties,
including
a
pyrazole
ring
phenyl
ring,
sequential
formation
two
C-N
three
C-C
bonds.
Organic Letters,
Год журнала:
2023,
Номер
25(39), С. 7214 - 7219
Опубликована: Сен. 26, 2023
A
novel
Rh(III)-catalyzed
cascade
alkenyl
C-H
activation/[3
+
2]
annulation/pinacol
rearrangement
reaction
of
enaminones
with
iodonium
ylides
has
been
developed.
This
methodology
provides
a
new
and
straightforward
synthetic
strategy
to
afford
highly
functionalized
2-spirocyclo-pyrrol-3-ones
in
satisfactory
yield
from
readily
available
starting
materials
under
mild
conditions.
Moreover,
gram-scale
reactions
further
derivatization
experiments
are
implemented
demonstrate
the
potential
utility
this
developed
approach.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7188 - 7198
Опубликована: Май 12, 2023
Rongalite
has
been
used
as
a
cheap
and
efficient
carbon
synthon
for
the
synthesis
of
divergent
N-heteroaromatics,
including
different
pyridines
quinolines.
The
selective
products
can
be
achieved
by
employing
enaminones
or
enaminones/anilines
reaction
partners.
In
addition,
compared
with
using
conventional
aldehyde
synthons,
rongalite
displays
an
evident
advantage
in
providing
considerably
higher
product
yields
under
milder
conditions.
GC-MS
analysis
process
performed
to
probe
possible
mechanism.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(2), С. 597 - 630
Опубликована: Ноя. 23, 2023
This
review
highlights
the
recent
progress
in
electrochemical
difunctionalization
of
alkenes
and
alkynes
involving
C–S/Se
bond
formation
to
access
organochalcogen
frameworks.
Organic Letters,
Год журнала:
2023,
Номер
25(47), С. 8451 - 8456
Опубликована: Ноя. 16, 2023
The
three-component
reactions
of
enaminones,
disulfides,
and
alcohols
for
the
synthesis
polyfunctionalized
alkenes
have
been
realized
via
C-H
C-N
bond
transformation
on
enaminones.
proceed
in
a
novel
"alkene-to-alkene"
difunctionalization
mode
without
using
any
transition
metal.
application
alkene
products
divergent
sulfenyl
heteroaryls,
including
sulfenylated
pyrazoles,
pyrimidines,
isoxazoles,
simple
annulation
has
also
verified.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(7), С. 4423 - 4437
Опубликована: Март 14, 2024
The
development
of
one-pot,
atom,
and
step-economic
new
methods
avoiding
metal,
harsh
reaction
conditions,
toxic
reagents
for
the
synthesis
medicinally
important
hybrid
molecules
bearing
more
than
one
bioactive
moieties
is
currently
hot
topics
in
organic
synthesis.
Herein,
we
report
a
green
efficient
room
temperature
multicomponent
novel
pyrazole-linked
thiazoles
involving
one-pot
C–C,
C–N,
C–S
bond-forming
process
from
aryl
glyoxal,
thioamide,
pyrazolones
1,1,1,3,3,3-hexafluoroisopropanol,
hydrogen
bond
donating
medium.
A
set
diverse
thiazole
pyrazole
were
prepared
good
to
excellent
yields
by
using
this
method.
This
methodology
can
also
be
extended
prepare
thiazole-linked
barbiturates
as
well
imidazole-linked
pyrazoles.
All
products
fully
characterized
spectroscopic
techniques.
notable
features
protocol
are
temperature,
metal
additive-free
use
recyclable
solvent,
water
byproduct,
wide
substrate
scope,
operational
simplicity,
easy
purification,
applicability
gram-scale
synthesis,
high
atom
economy,
presence
two
products.
