European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 30, 2024
Abstract
The
X−H
insertion
reaction
(X=heteroatom)
of
diazo
compounds
has
emerged
as
an
eminent
and
reliant
approach
for
the
construction
C−X
bonds.
By
merging
with
sequential
ring‐closing
transformations,
diverse
heterocyclic
systems
can
be
obtained
in
a
step‐economical
manner.
In
recent
years,
insertion/cyclization
cascades
one‐pot
transformations
attract
more
research
attention,
especially
area
asymmetric
synthesis.
Concentrating
on
assembly
N,O,S‐heterocycles,
this
Concept
elucidates
various
combinations
reactions
cyclization
via
addition
to
multiple
ring‐forming
strategies
reviewed
comprise
Michael‐type
Conia‐ene
reactions,
aldol
condensation,
Mannich
reaction.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(12), С. 2324 - 2338
Опубликована: Янв. 1, 2024
This
review
summarizes
the
most
recent
progress
made
in
C–H
bond
activation-initiated
spiroannulation
reactions
and
their
applications
construction
of
structurally
diverse
biologically
valuable
spirocyclic
scaffolds.
Cascade
annulation
reactions
can
assemble
structurally
intricate
polycyclic
molecules
from
simple
starting
materials
with
enhanced
efficiency
and
minimized
production
of
waste.
Presented
herein
is
a
concise
effective
synthesis
benzoisochromene
derivatives
based
on
C-H
activation-initiated
cascade
formal
[4+2]/[2+4]
aryl
enaminone
vinyl-1,3-dioxolan-2-one.
In
constructing
the
six-membered
carbocycle,
acted
as
C4
synthon
while
vinyl-1,3-dioxolan-2-one
C2
synthon.
O-heterocycle,
other
hand,
former
latter
C3O1
To
our
knowledge,
this
first
simultaneous
construction
both
carbocycle
an
O-heterocycle
via
concurrent
C-H/C-N/C-O
bond
cleavage
C-C/C-C/C-O
formation.
general,
novel
protocol
features
use
readily
obtainable
substrates
broad
scope,
excellent
atom-
step-economy,
intriguing
reaction
pathway,
valuable
products.
Organic Letters,
Год журнала:
2024,
Номер
26(35), С. 7425 - 7430
Опубликована: Авг. 22, 2024
Presented
herein
is
an
atom-
and
step-economical
method
enabling
the
precise
assembly
of
a
heptacyclic
scaffold
containing
both
azocine
indoline
units
through
cascade
reactions
indolin-1-yl(aryl)methanimines
with
diazo
indanediones.
The
formation
products
involves
C–H
bond
activation
double
carbene
insertion
followed
by
intramolecular
condensation,
retro-[2
+
2]
cycloaddition,
recyclization.
This
reaction
not
only
provided
concise
straightforward
strategy
for
synthesis
otherwise
difficult
to
obtain
compounds
from
readily
available
substrates
but
also
disclosed
unprecedented
mode
derivatives
compounds.
In
general,
this
novel
synthetic
protocol
has
advantages,
such
as
easily
obtainable
substrates,
structurally
sophisticated
products,
procedure,
good
compatibility
diverse
functional
groups,
ready
scalability.
Moreover,
thus
obtained
showed
decent
antiproliferative
activity
against
three
human
cancer
cell
lines.
Organic Letters,
Год журнала:
2024,
Номер
26(4), С. 786 - 791
Опубликована: Янв. 22, 2024
Presented
herein
is
an
unprecedented
synthesis
of
naphtho[1′,2′:4,5]furo[3,2-b]pyridinones
via
Ir(III)-catalyzed
C6/C5
dual
C–H
functionalization
N-pyridyl-2-pyridones
with
diazonaphthalen-2(1H)-ones.
This
protocol
forms
C–C
and
C–O
bonds
in
one
pot
which
diazonaphthalen-2(1H)-ones
serve
as
bifunctional
reagents,
providing
both
alkyl
aryloxy
sources.
To
the
best
our
knowledge,
this
first
example
title
compounds
by
using
substrates.
Notably,
method
features
operational
simplicity,
good
functional
group
tolerance,
high
efficiency,
atom
economy.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(6), С. 1811 - 1816
Опубликована: Янв. 1, 2024
An
efficient
protocol
to
construct
spiro[indole-3,4′-pyrazol]-5′-ones
via
ruthenium(
ii
)-catalyzed
selective
C–H
bond
activation/[4
+
1]
spirocyclization
starting
from
easily
available
N
-aryl
amidines
and
diazopyrazolones
has
been
developed.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 17, 2025
Functionalized
3,6-dihydro-2H-thiopyrans
are
synthesized
in
moderate
to
good
yields
from
α-diazo-β-diketones
and
vinylthiiranes
under
Cu(hfacac)2
catalysis
microwave
irradiation
via
[5
+
1]
annulation.
The
reaction
mechanism
includes
a
tandem
sequence
of
the
Cu-carbenoid
generation
α-diazo-β-diketones,
nucleophilic
attack
carbenoids,
subsequent
[2,3]-sigmatropic
rearrangement.
process
is
carbene-induced
ring
expansion
vinylthiiranes.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(15), С. 3372 - 3378
Опубликована: Май 29, 2024
Abstract
Presented
herein
is
a
switchable
synthesis
of
naphthalenone
spiroindanediones
or
4‐acyl‐1‐naphthols
via
condition‐controlled
divergent
cascade
reactions
aryl
enaminones
with
diazoindanediones.
When
the
reaction
was
carried
out
in
presence
an
oxidative
additive,
spiroindanedione
formed
through
C(
sp
2
)−H
alkylation
followed
by
simultaneous
spiroannulation
and
elimination
dimethylamine.
acid
on
other
hand,
4‐acyl‐1‐naphthol
ring
opening
moiety
attacked
situ
released
In
addition,
are
suitable
for
gram‐scale
applications
compatible
variety
substrates.
Moreover,
naphthol
products
allow
structural
elaborations
hybridization
drug,
thus
further
enhancing
value
this
developed
method.
