Chinese Journal of Organic Chemistry,
Год журнала:
2023,
Номер
43(9), С. 3006 - 3006
Опубликована: Янв. 1, 2023
As
one
of
the
most
important
structural
motifs
in
natural
compounds
and
active
pharmaceutical
ingredients,
azaspiro[4.5]trienonesderivatives
have
been
widely
used
field
organic
synthesis
due
to
their
excellent
properties
biological
activities.In
recent
years,
several
methods,
such
as
transition
metal
involvement,
visible
light
promotion,
metal-free
involvement
electrochemical
efficiently
construct
various
functional
groups
azaspiro[4.5]trienones.The
advances
azaspiro[4.5]trienones
are
reviewed,
representative
substrates
reaction
mechanisms
summarized
discussed.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(9), С. 1537 - 1542
Опубликована: Март 11, 2022
Abstract
Iron‐catalyzed
cascade
silyl
radical
addition/6‐
exo
‐trig
cyclization/dearomatization
of
biaryl
ynones
has
been
developed.
This
approach
uses
silane
as
the
precursor
well
silylation
reagent,
1,10‐phenanthroline
ligand,
and
tert
‐butyl
hydroperoxide
(TBHP)
oxidant.
By
employing
this
tandem
process,
a
series
silylated
spiro[5.5]trienones
were
prepared.
magnified
image
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7117 - 7127
Опубликована: Май 16, 2023
A
variety
of
acrylamides
holding
an
unactivated
N-benzyl
group
underwent
dearomative
ipso-cyclization
induced
by
sulfur-centered
radicals
(SCN/
SCF3/
SO2Ar)
in
the
presence
ceric
ammonium
nitrate
(CAN)
as
oxidant
to
furnish
azaspirocycles
good
yields.
This
is
first
report
on
ipso-dearomatization
that
proceeds
without
a
substituent
at
para-position
aromatic
ring.
The
developed
conditions
are
also
found
be
suitable
for
substrates
substituents
such
F,
NO2,
OMe,
OH,
and
OAc
para-position.
reaction
features
water
source
oxygen,
compatible
with
functional
groups,
short
time.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(12), С. 1399 - 1406
Опубликована: Фев. 29, 2024
Comprehensive
Summary
A
general
and
convenient
photoredox‐catalyzed
acylation
alkylcyanation
of
MBH
acetates
has
been
established,
enabling
the
assembly
C(sp
2
)–C(sp
3
)
bond
by
a
nitrogen‐centered
radical
strategy
for
synthesis
trisubstituted
alkenes
in
moderate
to
excellent
chemical
yields
(48
examples
total).
The
reaction
with
acyl
(indanone)
oxime
esters
afforded
containing
1,4‐dicarbonyl
groups.
Interestingly,
use
Eosin
Y
as
photocatalyst
catalytic
system
resulted
formation
distal
cyano
group‐anchored
via
deconstructive
functionalization
cycloketone
esters.
Notably,
these
resulting
compounds
could
be
applied
late‐stage
transformations,
providing
important
methods
dihydropyridazin‐3(2
H
)‐one.
Molecules,
Год журнала:
2023,
Номер
28(3), С. 1145 - 1145
Опубликована: Янв. 23, 2023
Radical
reactions
are
powerful
in
creating
carbon–carbon
and
carbon–heteroatom
bonds.
Designing
one-pot
radical
with
cascade
transformations
to
assemble
the
cyclic
skeletons
two
new
functional
groups
is
both
synthetically
operationally
efficient.
Summarized
this
paper
recent
development
of
involving
addition
cyclization
dienes,
diynes,
enynes,
as
well
arene-bridged
arene-terminated
compounds
for
preparation
difunctionalization
compounds.
Reactions
carried
out
initiators,
transition
metal-catalysis,
photoredox,
electrochemical
conditions
included.
Chemical Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
Radical-mediated
dearomatization
strategies
offer
a
blueprint
for
building
value-added
and
synthetically
valuable
three-dimensional
skeletons
from
readily
available
aromatic
starting
materials.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(34), С. 6879 - 6889
Опубликована: Янв. 1, 2022
An
unprecedented
copper-catalyzed
ipso-annulation
reaction
of
N-(p-methoxyaryl)propiolamides
with
1,3-diketones
has
been
developed,
which
enables
the
assembly
diketoalkylated
spiro[4.5]trienones
involving
oxidative
dearomatization
in
presence
ammonium
persulfate
[(NH4)2S2O8]
as
oxidant.
This
protocol
was
extended
to
biaryl
ynones,
efficiently
affording
spiro[5.5]trienones
good
yields.
The
significance
diketoalkyl
functionality
illustrated
by
further
transformation
into
3-pyrazoyl
spiro-trienone,
a
structurally
unique
motif.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(6), С. 4263 - 4272
Опубликована: Март 2, 2022
Heterocyclic
compounds,
especially
oxygen-containing
heterocyclic
are
crucial
moieties
in
bioactive
compounds
and
drug
leads.
Substituted
chroman-4-ones
a
kind
of
the
most
significant
structural
skeletons.
Herein,
we
report
visible-light-induced
dual
acylation
alkenes
for
constructing
3-substituted
chroman-4-ones,
which
undergoes
radical
tandem
cyclization
reaction
through
carbon–carbon
bond
cleavage
oxime
esters
by
nitrogen-centered
strategy.
A
series
were
prepared
with
up
to
86%
yield.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(16), С. 2772 - 2782
Опубликована: Июль 1, 2022
Abstract
We
have
disclosed
an
alkenes
dicarbofunctionalization
method
to
introduce
alkyl
and
electron‐rich
aryl
across
the
C=C
bond
of
styrenes
under
copper
catalyst
oxidative
conditions,
leading
construct
C(
sp
3
)‐C(
2
)/C(
)
bonds
via
dual
C−H
functionalization.
This
realizes
synthesis
1,1‐diarylalkanes,
which
are
very
important
skeleton
in
natural
products
drug
molecules,
through
grafting
aromatics,
including
indoles,
pyrroles,
trisubstituted
aromatic.
magnified
image
Green Synthesis and Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
A
visible-light-induced
brominated
spirocyclization
of
N-arylpropiolamides
and
CBr4
for
the
synthesis
3-bromo-azaspiro[4,5]trienones
is
reported
here.
This
process
allows
formation
C-Br,
C-C,
C=O
bonds
in
a
single
reaction
via
cascade
radical
addition/ipso-cyclization/oxidative
dearomatization
sequence.
protocol
also
features
high
functional
group
tolerance,
operational
simplicity
use
molecular
oxygen
as
an
oxidant
well
sustainable
photocatalyst-
additive-free
conditions
at
room
temperature.
Meanwhile,
presented
straightforward
strategy
has
been
applied
to
several
biologically
active
compounds.
