Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(8)
Опубликована: Июнь 16, 2022
Abstract
Indoles
are
extremely
important
and
versatile
building
blocks
in
the
field
of
chemistry.
This
review
highlights
advance
made
three‐component
reactions
indoles
between
2011–2021.
The
reaction
types
classified
into
three
categories
based
on
trigger
mechanisms.
Reactions
with
alkenes,
alkynes,
aldehydes,
imines,
ketones,
S,
Se,
etc
discussed.
In
order
to
highlight
mechanisms
involved,
this
has
provided
specific
analysis
inside
a
gray
box
each
scheme.
We
hope
these
studies
will
promote
future
research
indole
area.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(9), С. 2072 - 2078
Опубликована: Март 1, 2024
Abstract
A
photoinduced
direct
synthesis
of
3‐amino‐1‐indenones
via
radical
cascade
cyclization
strategy
is
demonstrated.
The
methodology
involves
a
domino
reaction
between
2‐alkynylarylnitrile
and
N
‐aminopyridinium
salt
captures
the
reactivity
in‐situ
generated
nitrogen‐centered
(NCR)
in
visible
light.
Multiple
bond‐forming
events
including
C−N,
C−C,
C−O
take
place
sequentially
on
enabling
construction
3‐amino‐1‐indenone
core
at
room
temperature
35–76%
yield.
preliminary
biological
screening
synthesized
compounds
indicative
their
potent
anti‐cancer
property.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 31, 2025
In
this
work,
we
studied
the
conjugated
additions
of
bis-trimethylsilylacetalketene
acetals
(bis-TMSKA)
to
para-quinone
methides
(p-QMs),
which
are
one
most
explored
molecules
for
study
and
gained
significant
attention
in
organic
chemistry
due
their
versatile
reactivity,
particularly
Michael
addition
reactions.
study,
trifluoromethanesulfonic
anhydride
(Tf2O)
was
used
as
an
activating
agent
p-QMs,
aiming
achieve
1,6-Michael
products
least
reported
1,8-Michael
with
pyridine
substituents.
The
reactivity
p-QMs
derived
from
demonstrated
distinct
reaction
pathways,
leading
formation
δ
γ
lactones.
investigation
also
involved
synthesizing
a
1-indanone
carboxylic
acids
obtained
1,6-addition.
A
visible
light-enabled
three-component
cascade
assembles
pyrrolopyrazoles
from
arylalkynes,
benzoquinones,
and
5-aminopyrazole
through
a
mechanistically
validated
carbonyl-alkyne
metathesis/(3
+
2)-cycloaddition/1,2-aryl
migration
sequence.
This
protocol
delivers
pyrrolopyrazole
heterocycles
in
up
to
96%
yield
with
excellent
functional
group
tolerance.
Preliminary
biological
screening
identified
promising
antitumor
activity
selected
products,
highlighting
the
potential
value
of
this
method.
The
proposed
reaction
mechanism
is
supported
by
control
experiments.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(7), С. 1453 - 1461
Опубликована: Янв. 1, 2022
The
directing
group
assisted
decarboxylative
ortho-benzoylation
of
N-aryl-7-azaindoles
with
α-keto
acids
has
been
achieved
by
synergistic
visible
light
promoted
photoredox
and
palladium
catalysis.
approach
tenders
rapid
entry
to
aryl
ketone
architectures
from
simple
acid
precursors
via
the
in
situ
generation
a
benzoyl
radical
intermediate.
transformation
provides
range
ortho-benzoylated
N-aryl-7-azaindoles,
excellent
site-selectivity
good
functional
compatibility
under
mild
reaction
conditions.
Biological
target
predictions
indicate
that
these
molecules
may
serve
as
potential
anti-cancer
anti-viral
agents.
New Journal of Chemistry,
Год журнала:
2022,
Номер
46(22), С. 10967 - 10973
Опубликована: Янв. 1, 2022
A
visible
light-mediated
approach
enabling
the
use
of
alcohols
as
nucleophiles
in
a
one-step
synthesis
α-alkoxy/hydroxy
diarylacetaldehydes
is
reported.
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(43)
Опубликована: Май 29, 2024
Visible-light-mediated
[2+2]
photocycloaddition
reaction
can
be
considered
an
ideal
solution
due
to
its
green
and
sustainable
properties,
is
one
of
the
most
efficient
methods
synthesize
four-membered
ring
motifs.
Although
research
on
alkynes
challenging
because
diminished
reactivity
alkynes,
more
significant
strain
products,
remarkable
achievements
have
been
made
in
this
field.
In
article,
we
highlight
recent
advances
visible-light-mediated
reactions
with
focus
mechanism
late-stage
synthetic
applications.
Advances
obtaining
cyclobutenes,
azetines,
oxetene
active
intermediates
continue
breakthroughs
fascinating
field
research.
Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(5)
Опубликована: Март 30, 2023
Abstract
Reported
here
is
a
general
visible‐light‐induced
Paternò‐Büchi
reaction
between
anthraquinones
and
olefins
lead
to
the
formation
of
diverse
anthraquinone‐based
spirocyclic
oxetanes
which
served
as
an
important
scaffold
in
natural
drugs
products.
This
approach
negates
need
for
UV
light,
thus
overcome
synthetic
limitations
traditional
reaction.
Therefore,
method
reported
characterized
by
high
regioselectivity,
simple
operations,
mild
conditions
broad
scope.
Chiral
ketones
and
their
derivatives
are
useful
synthetic
intermediates
for
the
synthesis
of
biologically
active
natural
products
medicinally
relevant
molecules.
Nevertheless,
general
broadly
applicable
methods
enantioenriched
acyclic
α,α-disubstituted
ketones,
especially
α,α-diarylketones,
remain
largely
underdeveloped,
owing
to
easy
racemization.
Here,
we
report
a
visible
light
photoactivation
phosphoric
acid–catalyzed
alkyne-carbonyl
metathesis/transfer
hydrogenation
one-pot
reaction
using
arylalkyne,
benzoquinone,
Hantzsch
ester
expeditious
α,α-diarylketones
with
excellent
yields
enantioselectivities.
In
reaction,
three
chemical
bonds,
including
C═O,
C─C,
C─H,
formed,
providing
de
novo
chiral
α,α-diarylketones.
Moreover,
this
protocol
provides
convenient
practical
method
synthesize
or
modify
complex
bioactive
molecules,
efficient
routes
florylpicoxamid
BRL-15572
analogs.
Computational
mechanistic
studies
revealed
that
C-H/π
interactions,
π-π
interaction,
substituents
all
play
crucial
roles
in
stereocontrol
reaction.
Bulletin of the Korean Chemical Society,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 17, 2024
Abstract
This
review
covers
the
visible
light
induced
reactions
of
quinones
such
as
benzoquinone,
naphthoquinone,
and
anthraquinone.
These
are
distinguished
by
their
fully
conjugated
structures,
which
feature
minimal
energy
gaps,
nonbonding
electron
pairs
on
oxygen
atoms.
Such
structural
attributes
facilitate
n
p
→
π*
transition,
allowing
for
easy
access
to
excited
states
rendering
highly
reactive
under
visible‐light
irradiation.
We
describe
three
primary
types
facilitated
these
electronic
characteristics:
Paternò–Büchi
(PB)
reactions,
entail
[2
+
2]
photocycloaddition
between
carbonyl
groups
alkenes
or
alkynes;
CH
activation
processes,
showcase
quinones'
versatility
in
functionalizing
hydrocarbons;
formation
donor–acceptor
complexes,
demonstrating
capability
engage
charge
transfer
interactions.
Through
this
review,
we
highlight
critical
role
play
photochemistry,
unique
properties,
broad
applicability
synthetic
organic
chemistry.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(18), С. 11939 - 11946
Опубликована: Авг. 30, 2022
Mild
and
efficient
ruthenium-catalyzed
hydroxy-arylation
of
the
terminal
double
bond
N-substituted
3-methyleneisoindolin-1-ones
is
described.
The
reaction
takes
place
with
aryl
diazonium
salt
as
arylating
reagent
water
hydroxyl
source
in
visible
light
at
ambient
temperature.
strategy
entails
vicinal
difunctionalization
alkene
enables
construction
3-benzyl-3-hydroxyisoindolin-1-one
heterocyclic
scaffolds
moderate
to
good
yields.
C-C
C-O
bonds
are
formed
one
pot
without
any
external
additive
oxidant
through
an
situ
generation
a
carbocation
intermediate
green
light.
