The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(23), С. 16330 - 16339
Опубликована: Ноя. 15, 2023
Bridged
isoxazolidines
were
synthesized
via
Rh(III)-catalyzed
C-H
allylation
of
α-aryl
nitrones
with
5-methylene-1,3-dioxan-2-one.
The
nitrone
group
serves
as
a
directing
and
1,3-dipole
in
the
activation/[3
+
2]
cycloaddition
cascade,
exhibiting
excellent
chemo-
stereoselectivity
along
good
functional
compatibility.
resulting
skeletal
structure
was
conveniently
modified
to
produce
range
important
chemical
frameworks,
protocol
applied
biologically
active
molecules.
RSC Advances,
Год журнала:
2024,
Номер
14(5), С. 2929 - 2946
Опубликована: Янв. 1, 2024
The
carbazole
scaffold
is
a
significant
entity
in
organic
compounds
due
to
its
variety
of
biological
and
synthetic
applications.
Traditionally,
skeletons
have
been
synthesized
either
via
the
Grabe-Ullman
method,
Clemo-Perkin
method
or
Tauber
method.
With
passage
time,
these
methods
modified
explored
accomplish
synthesis
target
compounds.
These
include
hydroarylations,
C-H
activations,
annulations
cyclization
reactions
mediated
by
catalysts
construct
carbazole-based
This
brief
review
article
intends
provide
recent
updates
on
important
methodological
developments
reported
for
nuclei
covering
2019-2023.
Catalysts,
Год журнала:
2025,
Номер
15(3), С. 279 - 279
Опубликована: Март 17, 2025
The
cyclization
of
propargyl
alcohols
with
CO2
represents
a
highly
significant
method
for
the
utilization
CO2.
resulting
cyclic
carbonates
possesses
high
chemical
value
and
hold
great
potential
applications
in
battery
electrolytes,
polymer
precursors,
pharmaceutical
intermediates.
However,
most
existing
reports
on
this
have
been
limited
to
simple
alcohol
substrates
that
are
substituted
inert
alkyl,
cycloalkyl,
phenyl
groups.
For
functionalized
alcohols,
such
as
alkyne-1,2-diols,
only
single
report
has
documented
thus
far.
In
study,
we
developed
an
innovative
catalytic
system
comprising
cost-effective
copper
salts
environmentally
friendly
ionic
liquids
(CuCl/1-ethyl-3-methylimidazolium
acetate)
alkyne-1,2-diols
Compared
previously
reported
AgF/bulky
monophosphine
ligand
(BrettPhos)
system,
our
is
free
traditional
volatile
solvents,
phosphine
ligands,
additives.
Notably,
first
Cu(I)-catalyzed
cyclization,
offering
advantages
terms
cost-effectiveness
reduced
toxicity
compared
silver
salts.
Moreover,
use
ensures
considerable
recyclability,
further
enhancing
sustainability
practicality
approach.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(18), С. 13315 - 13326
Опубликована: Сен. 5, 2023
The
site-selective
modification
of
quinazolinone
as
a
privileged
bicyclic
N-heterocycle
is
an
attractive
topic
in
medicinal
chemistry
and
material
science.
We
herein
report
the
ruthenium(II)-catalyzed
C-H
allylation
2-aryl
quinazolinones
with
2-methylidene
cyclic
carbonate.
In
addition,
tandem
annulation
are
achieved
under
rhodium(III)
catalysis,
resulting
formation
tetracyclic
including
tertiary
carbon
center.
Post-transformations
synthesized
products
demonstrate
potential
developed
methodology.
A
series
mechanistic
investigations
were
also
performed.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 19, 2024
Abstract
Herein
we
report
for
the
first
time
a
sunlight‐driven,
irreversible
photocyclization
reaction
of
indole‐linked
trisubstituted
thiazoles,
synthesis
highly
fluorescent
thiazole‐fused
benzo[
]carbazoles
using
mixture
solvents
(CH
3
CN:
DMSO;
:
1).
Ring
opening
indole
moiety
was
observed
in
case
thiazole
derivatives
having
2‐methyl
substituents.
Under
similar
conditions,
thiazoles
cyclic
1,3‐dicarbonyls
place
also
worked.
This
provides
products
two
medicinally
important
moieties
and
benzocarbazoles.
We
have
studied
photophysical
properties
all
found
that
most
synthesized
very
good
fluorescence
quantum
yields.
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
42(9), С. 985 - 989
Опубликована: Дек. 26, 2023
Comprehensive
Summary
A
Ru(II)‐catalyzed
ortho
allylation
reaction
of
N
‐aryl‐7‐azaindole
with
readily
available
2‐methylidene
cyclic
carbonate
has
been
developed.
This
is
an
effective
pathway
for
synthesizing
7‐azaindole
derivatives
a
wide
scope
substrates
and
high
yields.
In
addition,
the
method
can
be
extended
to
other
heterocyclic
compounds
several
carbonates,
highlighting
practicality
this
strategy
synthesis.
A
unique
catalyst-controlled
chemodivergent
strategy
to
access
2-vinyl
indolines
and
indole-2-acetates
by
overcoming
the
usual
allylic
reactivity
of
vinyl
ethylene
carbonates
(VECs)
via
a
tandem
C-H/C-O
bond
activation
sequence
is
disclosed
herein.
This
methodology
provides
useful
molecular
scaffolds
following
two
distinct
pathways
in
highly
step-
atom-economical
manner.
The
pathway
features
challenging
beta-hydroxide
elimination
Rh-catalyzed
transformation,
we
have
observed
unusual
competing
such
as
an
oxidative
insertion
MeOH
into
Rh(III)
give
putative
Rh(V)-H
intermediate.
Mechanistic
insights
unveil
new
mode
open
avenue
for
divergent
catalysis.
Post
synthetic
modification
annulated
products
add
additional
advantage
methodology.
The
synthesis
of
(iso)quinoline-indole
hybrids
by
reacting
(iso)quinoline
N-oxides
with
o-alkynylanilines
in
the
presence
a
combination
copper(II)
catalyst
and
bidentate
2,2′-bipyridine
ligand
is
described.
utility
this
method
was
demonstrated
through
site-selective
functionalization
synthesized
products.
A
plausible
reaction
pathway
for
amination
followed
annulative
indole
formation
elucidated
series
mechanistic
investigations.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(23), С. 5978 - 5985
Опубликована: Янв. 1, 2023
An
FeCl
3
-catalyzed
AB
2
three-component
reaction
of
indole-2-carbaldehydes
and
5-aminopyrazoles
was
established
for
the
synthesis
indolo[3,2-
b
]carbazoles.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(23), С. 4241 - 4247
Опубликована: Окт. 30, 2023
Abstract
Complex
spirocyclic
isoindolines
and
pyrrolidines
are
formed
in
a
tandem
process
involving
Co(III)‐catalyzed
dienylation
of
cyclic
C‐aryl
nitrones
with
2,3‐butadien‐1‐ol
carbonates,
followed
by
intramolecular
1,3‐dipolar
cycloaddition.
The
nitrone
moiety
serves
both
as
directing
group
for
the
C(aryl)−H
activation
dipole
cycloaddition
step.
High
regioselectivity
fused
vs.
bridged
product
can
be
obtained
adjusting
reaction
temperature.
Reactions
substituted
allenic
substrates
provide
heterocycles
additional
stereocenters
usually
complete
diastereoselectivity.
products
were
readily
transformed
further
into
other
complex
nitrogen‐containing
systems.
Bulletin of the Korean Chemical Society,
Год журнала:
2023,
Номер
45(2), С. 131 - 144
Опубликована: Дек. 12, 2023
Abstract
The
synthesis
and
functionalization
of
privileged
nitrogen
heterocycles
has
emerged
as
a
central
topic
in
drug
discovery
material
science.
In
this
context,
the
tandem
C–H
intramolecular
annulation
received
prodigious
attention,
it
is
able
to
expedite
construction
heteroaromatic
frameworks
beyond
conventional
functionalization.
general,
significant
effort
been
made
develop
[3
+
2]
dipolar
cycloaddition
azomethine
imines
with
π‐unsaturated
compounds.
Moreover,
3],
[4
2
2],
[5
3]
reactions
various
dipolarophiles
have
demonstrated.
To
date,
however,
combination
catalytic
cyclization
using
both
directing
groups
units
less
explored.
This
review
focuses
on
recent
progress
toward
azomethines
range
coupling
partners.
