Angewandte Chemie,
Год журнала:
2023,
Номер
136(1)
Опубликована: Ноя. 16, 2023
Abstract
The
concept
of
a
domino‐type
reaction
has
been
applied
in
wide
range
fields
such
as
synthetic
organic
chemistry,
material
engineering,
and
life
science.
To
extend
the
domino
to
redox
we
designed
synthesized
dimeric
quinodimethane
(QD)
with
nonplanar
dithiin
spacer.
domino‐redox
properties
can
be
activated
by
raising
temperature,
based
on
thermally
equilibrated
twisted
conformation
QD,
which
higher
HOMO
level
that
is
more
readily
oxidized.
After
one
QD
unit
oxidized
(trigger),
steric
repulsion
electronic
interaction
between
electrophores
make
neighboring
adopt
(domino
process),
facilitates
following
oxidation.
Thus,
was
achieved
for
first
time
change
due
drastic
molecular
conformation.
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.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(15)
Опубликована: Март 15, 2023
Abstract
A
simple
base‐promoted
[2+1]
annulation
of
indolin‐3‐ones
and
bromosulfonium
salts
has
been
developed
in
this
article.
This
strategy
uses
easily
prepared
1
as
C1
synthons
2
C2
under
mild
reaction
conditions,
33
examples
C2‐spirocyclopropyl‐indolin‐3‐ones
were
obtained
with
up
to
99
%
yield
>20
:
dr.
Molecules,
Год журнала:
2022,
Номер
27(22), С. 8051 - 8051
Опубликована: Ноя. 19, 2022
In
this
work
a
microwave-assisted
Knoevenagel/Michael/cyclization
multicomponent
domino
methodology,
using
ethanol
as
solvent
and
the
ionic
liquid
1-methylimidazolium
chloride
catalyst
was
developed
for
synthesis
of
spiro
compounds.
The
reaction
conditions
considered
ideal
were
determined
from
methodological
study
varying
solvent,
catalyst,
amount
temperature,
heating
mode.
Finally,
generality
methodology
evaluated
by
exploring
scope
reaction,
starting
materials
(isatin,
malononitrile,
barbituric
acid).
Overall,
twelve
compounds
synthesized
in
good
yields
(43-98%)
X-ray
structure
compound
1b
obtained.
addition,
vitro
antiproliferative
activities
spirocycles
against
four
types
human
cancer
cell
lines
including
HCT116
(human
colon
carcinoma),
PC3
(prostate
HL60
(promyelocytic
leukemia),
SNB19
(astrocytoma)
screened
MTT-based
assay.
It
is
noteworthy
that
1c
inhibited
tested
with
lowest
IC50
values:
52.81
µM
HCT116,
74.40
PC3,
101
SNB19,
49.72
HL60.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(3), С. 1803 - 1814
Опубликована: Янв. 12, 2023
Spiro
compounds
have
been
considered
key
scaffolds
for
pharmaceutical
applications.
Although
many
synthetic
methods
exist
monospirocycles,
fewer
approaches
are
known
dispirocycles.
Here,
we
report
a
highly
cis-selective
method
constructing
5/6/5-dispirocyclic
structure
containing
pyrrolidine
and
γ-lactam
rings
with
various
substituents
from
series
of
N-arylpropiolamides.
The
high
cis-selectivity
would
result
isomerization
under
thermodynamic
control.
Cis-
trans-diastereomers
can
be
in
equilibrium,
favoring
cis-adducts.
Organic Letters,
Год журнала:
2023,
Номер
25(20), С. 3790 - 3795
Опубликована: Май 15, 2023
Merrifield
resin-anchored
pyridines
were
prepared
and
applied
as
reusable
mediators
for
trans-selective
cascade
synthesis
of
2,3-dihydroindoles.
The
developed
approach
relied
on
in
situ
N-ylide
formation
followed
by
Michael
substitution
reactions.
reaction
was
also
carried
out
efficiently
with
simple
pyridine.
products
further
transformed
into
synthetically
valuable
compounds,
supported
pyridine
reused
multiple
cycles.
Density
functional
theory
calculations
confirmed
the
trans-selectivity
lower-energy
pathway.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(19), С. 13204 - 13223
Опубликована: Сен. 14, 2022
-heterospirocycles
are
interesting
structural
units
found
in
both
natural
products
and
medicinal
compounds
but
have
relatively
few
reliable
methods
for
their
synthesis.
Here,
we
enlist
the
photocatalytic
generation
of
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
63(1)
Опубликована: Ноя. 16, 2023
The
concept
of
a
domino-type
reaction
has
been
applied
in
wide
range
fields
such
as
synthetic
organic
chemistry,
material
engineering,
and
life
science.
To
extend
the
domino
to
redox
we
designed
synthesized
dimeric
quinodimethane
(QD)
with
nonplanar
dithiin
spacer.
domino-redox
properties
can
be
activated
by
raising
temperature,
based
on
thermally
equilibrated
twisted
conformation
QD,
which
higher
HOMO
level
that
is
more
readily
oxidized.
After
one
QD
unit
oxidized
(trigger),
steric
repulsion
electronic
interaction
between
electrophores
make
neighboring
adopt
(domino
process),
facilitates
following
oxidation.
Thus,
was
achieved
for
first
time
change
due
drastic
molecular
conformation.
Synlett,
Год журнала:
2022,
Номер
34(09), С. 1063 - 1067
Опубликована: Дек. 28, 2022
Abstract
When
irradiated
with
visible
light,
various
cyclic
2-alk-4-enyl-substituted
1,3-diketones
undergo
an
intramolecular
endo-addition
(m
=
1)
onto
the
double
bond
resulting
in
spirocyclic
products
(11
examples,
62–92%
yield).
Both
organic
(TXT:
thioxanthone,
20
mol%)
and
organometallic
Ir-based
photocatalyst
(5
promote
reaction.
Addition
of
triisopropylthiophenol
is
required
to
secure
high
yields.
The
spirocyclization
a
2-alk-5-enyl-substituted
substrate
2)
delivers
mixture
seven-membered
endo-
six-membered
exo-cyclization
products.
