Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
366(1), P. 141 - 147
Published: Nov. 28, 2023
Abstract
Presented
herein
is
a
synthesis
of
indane
fused
bicyclic
pyrazolidinones
based
on
the
reactions
aryl
azomethine
imines
with
cyclopropanols.
Mechanistically,
formation
product
involves
Rh(III)‐catalyzed
direct
C(
sp
2
)−H
alkylation
imine
cyclopropanol
through
in
situ
ring‐opening,
followed
by
cascade
intramolecular
C
‐
and
N
‐nucleophilic
addition.
In
this
tandem
process,
acts
as
not
only
an
alkylating
agent
but
also
masked
nucleophile
electrophile
to
participate
construction
both
pyrazolidinone
scaffolds.
To
our
knowledge,
such
reaction
pattern
has
been
disclosed.
general,
synthetic
protocol
advantages
easily
obtainable
substrates,
valuable
products,
concise
procedure,
unique
pathway,
good
compatibility
diverse
functional
groups.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(12), P. 2324 - 2338
Published: Jan. 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.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(24), P. 4422 - 4428
Published: June 8, 2023
Presented
herein
is
a
condition-controlled
selective
synthesis
of
pyranone-tethered
indazoles
or
carbazole
derivatives
via
the
cascade
reactions
N-nitrosoanilines
with
iodonium
ylides.
Mechanistically,
formation
former
involves
an
unprecedented
process
including
nitroso
group-directed
C(sp2)–H
bond
alkylation
N-nitrosoaniline
ylide
followed
by
intramolecular
C-nucleophilic
addition
to
moiety,
solvent-assisted
cyclohexanedione
ring
opening,
and
transesterification/annulation.
On
contrary,
latter
initial
annulation
denitrosation.
These
developed
protocols
feature
easily
controllable
selectivity,
mild
reaction
conditions,
clean
sustainable
oxidant
(air),
valuable
products
that
are
structurally
diverse.
In
addition,
utility
was
showcased
their
facile
diverse
transformations
into
synthetically
biologically
interesting
compounds.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(3), P. 1880 - 1897
Published: Jan. 22, 2024
Herein,
we
present
an
efficient
synthesis
of
1,7-fused
indolines
tethered
with
a
spiroindolinonyl
moiety
through
the
cascade
reaction
indolin-1-yl(aryl)methanimines
diazo
oxindoles.
To
best
our
knowledge,
this
is
first
example
in
which
indoline
skeleton
was
constructed
along
simultaneous
introduction
spiro
element
initiated
by
C–H
bond
activation
indoline.
In
forming
title
product,
substrate
and
coupling
partner
demonstrated
unprecedented
pattern
latter
acts
as
C1
synthon
to
participate
construction
spirocyclic
scaffold
reductive
elimination
key
seven-membered
Ru(II)
species
using
air
effective
sustainable
oxidant
regenerate
active
catalyst.
Moreover,
studies
on
cytotoxicity
selected
products
against
several
human
cancer
cell
lines
their
potential
lead
compounds
for
development
anticancer
drugs.
With
notable
features
such
simple
economical
substrates,
pharmaceutically
valuable
sophisticated
skeleton,
mild
conditions,
cost-free
oxidants,
high
efficiency,
excellent
compatibility
diverse
functional
groups,
scalability,
method
expected
find
wide
applications
related
areas.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(5), P. 1191 - 1197
Published: Jan. 1, 2023
In
this
paper,
we
present
a
direct,
effective
and
atom-economical
access
toward
quinoline-fused
cyclobutane
derivatives
through
Rh(
iii
)-catalyzed
cascade
reactions
of
N
-arylsydnones
with
allenyl
acetates.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(35), P. 7425 - 7430
Published: Aug. 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.
RSC Advances,
Journal Year:
2024,
Volume and Issue:
14(21), P. 14539 - 14581
Published: Jan. 1, 2024
The
synthesis
of
dihydrobenzofuran
scaffolds
bears
pivotal
significance
in
the
field
medicinal
chemistry
and
organic
synthesis.
These
heterocyclic
hold
immense
prospects
owing
to
their
significant
pharmaceutical
applications
as
they
are
extensively
employed
essential
precursors
for
constructing
complex
frameworks.
Their
versatility
importance
make
them
an
interesting
subject
study
researchers
scientific
community.
While
exploring
synthesis,
have
unveiled
various
novel
efficient
pathways
assembling
core.
In
wake
extensive
data
being
continuously
reported
each
year,
we
outlined
recent
updates
(post
2020)
on
methodological
accomplishments
employing
catalytic
role
several
transition
metals
forge
functionalities.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(4), P. 1015 - 1021
Published: Jan. 1, 2023
Presented
herein
is
a
divergent
synthesis
of
indene-fused
pyrazoles
and
bridged
benzodiazepines
tethered
with
hydroxymethyl
group
through
the
cascade
reactions
aryl
azomethine
imines
vinyl
cyclic
carbonates.
Chinese Journal of Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 27, 2025
Comprehensive
Summary
Presented
herein
is
a
condition‐controlled
selective
synthesis
of
CF
3
‐chromene
and
‐benzofuran
based
on
the
reaction
N
‐phenoxyacetamide
‐ynone.
When
carried
out
in
MeOH
under
catalysis
Rh(III),
formed
via
C—H
metalation‐initiated
alkenylation,
acetamide
group
migration
intramolecular
oxo
‐nucleophilic
addition.
On
other
hand,
when
run
DMSO
promotion
CsOAc,
generated
aza
‐Michael
addition‐initiated
[3,3]‐σ
rearrangement,
addition
water
elimination.
To
our
knowledge,
this
first
report
construction
chromene
or
benzofuran
scaffold
along
with
introduction
unit
from
same
starting
materials.
The
methodology
was
scalable
products
could
be
readily
transformed
into
valuable
products.
Moreover,
thus
obtained
possess
decent
anticancer
activity.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(17), P. 12641 - 12657
Published: Aug. 17, 2023
Presented
herein
is
an
effective
and
sustainable
synthesis
of
O-heterocycle
spiro-fused
cyclopentaquinolinone
cyclopentaindene
derivatives
through
light-driven
cascade
reactions
N-(o-ethynylaryl)acrylamides
or
2-(2-(phenylethynyl)benzyl)acrylate
with
various
O-heterocycles.
Experimental
mechanistic
studies
revealed
that
these
are
initiated
by
visible
light-induced
radical
formation
from
its
regioselective
addition
onto
the
acrylamide
acrylate
moiety
followed
6-exo-dig
5-endo-trig
annulation,
which
terminated
single
electron
oxidation
proton
elimination.
Compared
previously
reported
synthetic
methods
for
similar
purposes,
this
newly
developed
protocol
has
advantages
such
as
a
broad
substrate
scope,
extremely
mild
reaction
conditions,
excellent
atom-economy,
high
efficiency,
good
compatibility
diverse
functional
groups.
With
all
merits,
method
expected
to
find
wide
applications
in
related
research
arena.
