Tandem [4C + 2C] cyclization reaction of α-acetyl-α-oxo ketene dithioacetals and acrylonitrile: A straightforward synthesis of polysubstituted cyclohex-3-enones
Synthetic Communications,
Год журнала:
2025,
Номер
unknown, С. 1 - 12
Опубликована: Апрель 26, 2025
Язык: Английский
NaOH promoted hydrolysis of α-oxo ketene- N, S -acetals: Effective synthesis of β-keto amides
Synthetic Communications,
Год журнала:
2024,
Номер
54(4), С. 312 - 320
Опубликована: Янв. 2, 2024
An
effective
and
novel
synthesis
of
β-keto
amides
had
been
developed
by
NaOH
promoted
hydrolysis
α-oxo
ketene-N,
S-acetals.
It
was
found
that
the
S-acetals
in
presence
2
equivalent
refluxing
EtOH
(95%)
gave
excellent
yields.
The
uses
toxic
harmful
amines
as
well
prepurification
these
nucleophilic
reagents
were
not
required
reaction.
method
can
extend
to
gram
scale.
Язык: Английский
Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates
European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(42)
Опубликована: Сен. 5, 2022
Abstract
Recursive
Anionic
Cyclization
(RAC)
continues
to
proliferate
as
a
mechanistically
distinct
domino
strategy.
Deployment
of
nitroalkanes
source
recursive
carbanions
has
created
niche
operating
space
for
generating
molecular
complexity
and
diversity.
This
new
corollary
i.
e.
nitronate
cyclization
is
the
basis
[5
C+1
C]
strategy
wherein
act
one‐carbon
lynchpin,
providing
rapid
access
topologically
intriguing,
densely
functionalized
carbo‐
heterocycles
embodying
multiple
chiral
centers
with
regio‐,
stereo‐
enantioselectivity.
Extension
aromatic
domains,
particularly
via
benzannulation
reactions,
further
consolidated
space.
While
leveraging
functional
versatility
nitro
group
post‐domino
modifications,
such
endeavors
have
culminated
in
total
synthesis
diverse
natural
products.
An
incisive
analysis
cyclizations
their
emergent
potentials
delineated
this
review.
It
hoped
that
focused
narrative
will
enthuse
draw
practitioners
arena
advance
field.
Язык: Английский
HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(9), С. 1413 - 1418
Опубликована: Апрель 12, 2023
Abstract
Hexafluoroisopropanol
(HFIP)
has
been
extensively
applied
in
organic
synthesis
as
a
versatile
reaction
media.
However,
the
application
of
HFIP
an
catalyst
rarely
studied.
Presented
here,
is
example
HFIP‐catalyzed
Mannich‐type
between
quinoxalin‐2(1
H
)‐ones
and
difluoroenoxysilanes.
The
developed
protocol
tolerates
various
substituents
under
mild
conditions,
providing
divergent
approach
to
construction
difluoro‐substituted
3,4‐dihydroquinoxalin‐2(1
monofluoroquinoxalin‐2(1
51–92%
yields.
magnified
image
Язык: Английский
[2+2+1+1] Cycloaddition for de novo Synthesis of Densely Functionalized Phenols
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(36)
Опубликована: Июль 10, 2023
A
unique
benzannulation
strategy
for
regioselective
de
novo
synthesis
of
densely
functionalized
phenols
is
described.
Through
metal-mediated
formal
[2+2+1+1]
cycloaddition
two
different
alkynes
and
molecules
CO,
a
series
were
obtained.
The
allows
efficient
installation
up
to
five
substituents
on
phenol
ring.
resulting
have
substitution
pattern
from
those
obtained
Dötz
Danheiser
benzannulations.
Язык: Английский
Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides
Beilstein Journal of Organic Chemistry,
Год журнала:
2024,
Номер
20, С. 2225 - 2233
Опубликована: Сен. 3, 2024
An
eco-friendly
selective
hydrolysis
of
chain
α-oxo
ketene
N
,
S
-acetals
in
water
for
the
switchable
synthesis
β-keto
thioesters
and
amides
is
reported.
In
refluxing
water,
reactions
presence
1.0
equiv
dodecylbenzenesulfonic
acid
effectively
afforded
excellent
yield,
while
were
successfully
obtained
yield
when
carried
out
3.0
NaOH.
The
green
approach
to
avoids
use
harmful
organic
solvents,
thiols
thiolacetates
as
well
amines,
which
could
result
serious
environmental
safety
issues.
Язык: Английский
K2CO3-accelerated amidation of carboxylic acids using α-oxo ketene-N,S-acetals as amine surrogates
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
10(3), С. 686 - 698
Опубликована: Дек. 7, 2022
A
novel
and
efficient
K
2
CO
3
-accelerated
amidation
of
carboxylic
acids
with
α-oxo
ketene-
N
,
S
-acetals
as
amine
surrogates
is
developed.
Язык: Английский
Catalyst- and additive-free [3 + 3] cyclization–aromatization of β,γ-dioxobutanoate with amines for synthesis ofp-aminophenols
Green Chemistry,
Год журнала:
2022,
Номер
24(24), С. 9690 - 9696
Опубликована: Янв. 1, 2022
A
[3
+
3]
cyclization–aromatization
of
β,γ-dioxobutanoate
with
amines
for
synthesis
p
-aminophenols
under
catalyst-
and
additive-free
conditions
was
developed.
The
reaction
displays
high
efficiency
in
the
late-stage
modification
drug
molecules.
Язык: Английский
Transition-metal-free decarbonylation–oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones
Bhaskar B. Dhotare,
Seema V. Kanojia,
Chahna K Sakhiya
и другие.
Beilstein Journal of Organic Chemistry,
Год журнала:
2024,
Номер
20, С. 2655 - 2667
Опубликована: Окт. 21, 2024
A
transition-metal-free
decarbonylation–oxidation
protocol
for
the
conversion
of
3-arylbenzofuran-2(3
H
)-ones
to
2-hydroxybenzophenones
under
mild
conditions
has
been
developed.
NMR
studies
confirmed
role
in-situ-generated
hydroperoxide
in
conversion.
The
was
applied
a
diverse
range
substrates
access
target
products
good
excellent
yields.
structure–activity
study
5-substituted-2-hydroxybenzophenones
towards
UV-protection
abilities
verified
by
mathematical
calculations.
Язык: Английский
[2+2+1+1] Cycloaddition for de novo Synthesis of Densely Functionalized Phenols
Angewandte Chemie,
Год журнала:
2023,
Номер
135(36)
Опубликована: Июль 10, 2023
Abstract
A
unique
benzannulation
strategy
for
regioselective
de
novo
synthesis
of
densely
functionalized
phenols
is
described.
Through
metal‐mediated
formal
[2+2+1+1]
cycloaddition
two
different
alkynes
and
molecules
CO,
a
series
were
obtained.
The
allows
efficient
installation
up
to
five
substituents
on
phenol
ring.
resulting
have
substitution
pattern
from
those
obtained
Dötz
Danheiser
benzannulations.
Язык: Английский