Organic Letters,
Год журнала:
2024,
Номер
26(45), С. 9752 - 9758
Опубликована: Ноя. 6, 2024
We
developed
a
protocol
for
the
synthesis
of
functionalized
pyrrolo[2,1-a]isoquinoline
derivatives
(PIQDs)
3
from
enaminones
1
using
vinylene
carbonate
2.
This
strategy
involved
[3
+
2]
and
[4
cycloadditions
via
heating
mixture
substrates
with
2
DCE
at
60
°C,
catalyzed
by
[Cp*RhCl2]2
oxidized
Cu(OAc)2
AgSbF6
promoted
NaOAc.
As
we
increased
reaction
temperature
to
110
°C
under
same
conditions,
synthesized
PIQDs
4
through
sequential
C–H
activation,
alkene
insertion,
migratory
C–N
reductive
elimination,
β-O
finally
dehydration.
result,
series
3–4
were
generated
forming
four
bonds
(2
C–C
bonds)
in
single
step.
realizes
linear
molecules
potential
biological
activity,
specifically
natural-like
heterocycles
(3–4).
It
expands
application
as
C2
synthon
construction
pyrrole
isoquinoline
skeletons
combinatorial
parallel
syntheses
one-pot
reactions.
We
present
an
efficient
silver-catalyzed
one-pot
controllable
molecular
editing
protocol
for
the
transformation
of
2-amino-N-substituted
benzamides
into
6-selenylated
N-substituted
1,2,3-benzotriazine-4(3H)-ones
under
mild
reaction
conditions.
This
three-component
strategy
is
achieved
by
building
N-N/N═N/C-Se
bonds,
which
provides
a
practical
pathway
preparation
selenylated
with
broad
substrate
scope
and
good
functional
group
tolerance,
as
well
high
site-selectivity.
Mechanistic
experiments
suggest
that
this
proceeds
via
intermolecular
site-selective
C-H
selenylation
readily
available
diselenides,
followed
annulation
using
AgNO3
nitrogen
synthon.
Molecules,
Год журнала:
2025,
Номер
30(6), С. 1194 - 1194
Опубликована: Март 7, 2025
A
novel,
eco-friendly,
and
efficient
method
for
constructing
2,3-disubstituted
chromone
skeletons
from
readily
available
water,
o-hydroxyaryl
enaminones
(o-HPEs),
aryldiazonium
salts
has
been
developed
under
mild
reaction
conditions.
This
α,β-C(sp2)–H
bond
difunctionalization/chromone
annulation
strategy
is
achieved
by
building
two
C(sp3)–O
bonds
a
C(sp2)-N
bond,
which
provides
practical
pathway
the
preparation
of
2-hydroxy-3-hydrazono-chromones
in
moderate
to
excellent
yields,
enabling
broad
substrate
scope
good
functional
group
tolerance,
as
well
gram-scale
synthesis.
protocol
offers
valuable
tool
synthesizing
diverse
functionalized
chromones
with
potential
applications
drug
discovery
industrial
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 6, 2025
A
water-controlled
geminal
phosphinoylation
of
enaminones
with
H-phosphine
oxides
has
been
established
through
AlCl3-mediated
C-N
bond
cleavage
in
this
work,
which
provides
a
novel
strategy
for
accessing
various
hydroxy
and
diphosphinoyl
products
3a
4a
high
yields.
The
transformation
features
excellent
functional
group
tolerance,
operational
simplicity,
atom
economy,
is
amenable
complex
molecule
skeletons.
Preliminary
mechanism
studies
suggest
the
conversion
from
to
involve
elimination
hydroxyl
group,
water
temperature
plays
critical
role
influencing
reaction
pathway
product
selectivity.
This
research
significant
value
functionalization
enaminones.
Abstract
A
facile
Cu(II)‐catalyzed
annulation
of
o
‐phenylenediamine
and
phenacyl
bromides
in
EtOH
has
been
developed.
In
this
protocol,
diverse
2‐functionalized
quinoxalines
were
prepared
74%–91%
yields
with
high
chemoselectivity.
The
salient
features
are
the
excellent
yields,
broad
substrate
scope,
mild
reaction
conditions,
large‐scale
preparation.
This
not
only
fills
gap
conventional
metal‐catalyzed
o‐phenylenediamine
but
also
provides
a
practical
strategy
for
construction
quinoxalines.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 19, 2025
Herein,
we
present
a
protocol
for
the
construction
of
functionalized
quinolines,
i.e.,
3-acyl-4-(2,2,2-trifluoro-ethyl)quinolines
(ATFQLs)
4,
from
ortho-vinyl
enaminones
and
1-(trifluoromethyl)-1,3-benzo-[d][1,2]-iodaoxol-3(1H)-one,
which
was
catalyzed
by
FeCp2
promoted
FeCl3
(Lewis
acid)
additives
in
solvents
(i.e.,
acetonitrile
toluene).
This
strategy
first
utilized
FeCp2-catalyzed
functionalization
alkenes
with
trifluoromethyl
radicals.
The
intermediate
formed
captured
ortho-iodobenzoate
substrate,
yielding
3,
then
underwent
FeCl3-catalyzed
elimination
at
higher
temperature
to
form
an
α,β-unsaturated
intermediate.
subsequent
intramolecular
Michael
reaction
yielded
final
target
compound
4.
In
summary,
series
ATFQLs
4
were
synthesized
through
formation
two
bonds
(C═C
C-C).
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 10, 2024
Comprehensive
Summary
Two
reaction
modes
for
metal‐free
[3
+
2]
cyclization
of
N
‐aminopyridinium
derivatives
with
β
‐alkoxyvinyl
trifluoromethylketones
have
been
described
through
selective
C—O
or
C—O/C—C
bond
cleavage.
This
strategy
can
also
be
extended
to
the
enaminones
and
bromoalkynes.
A
broad
range
‐aminopyridinium,
‐aminoquinolinium,
‐aminoisoquinolinium
salts
are
well
tolerated,
enabling
divergent
synthesis
trifluoroacylated,
non‐substituted,
acylated,
brominated
pyrazolo[1,5‐
a
]pyridine
(62
examples).
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 14, 2024
Abstract
A
novel
and
practical
zinc‐catalysed
synthesis
of
1
H
‐pyrazole
has
been
developed.
The
one‐pot
protocol
enables
the
cycloaddition
enaminone
tosylhydrazide
via
C−N
S−N
bond
breaking
process,
leading
to
diverse
mono‐substituted
pyrazole
derivatives
in
high
yields.
Moreover,
easily
accessible
materials,
broad
substrate
scope
with
excellent
functional
group
tolerance,
ease
isolation
open‐air
conditions
are
key
features
present
method.
