A
general
protocol
for
the
synthesis
of
a
variety
functionalized
quinazolinones
has
been
developed
through
sequential
Pd-catalyzed
coupling/1,5-alkyloxy/thio/azole
shift/6π
electrocyclization
reaction
isocyanides
and
2-carbonylaryl
azides.
When
3-(2-isocyanoethyl)indoles
were
utilized,
an
unusual
competitive
between
[1,5]-shift
indole-spirocyclization
was
observed,
which
renders
modular
spiroindolenine-3,3'-pyrrolo[2,1-
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.
Future Medicinal Chemistry,
Год журнала:
2025,
Номер
unknown, С. 1 - 17
Опубликована: Март 29, 2025
Lung
cancer
is
the
most
prevalent
invasive
malignancy
and
leading
cause
of
cancer-related
death.
Chemotherapy
vital
for
lung
therapy,
but
multidrug
resistance
responsible
majority
fatalities,
creating
an
imperative
demand
to
develop
novel
chemotherapeutics.
Indole
a
valuable
anti-lung
pharmacophore
since
its
derivatives
could
act
on
cells
through
various
mechanisms.
Notably,
indole
hybrids
inhibit
multiple
targets
simultaneously
have
potential
overcome
shortcomings
traditional
Moreover,
many
such
as
indole-pyrimidine
hybrid
osimertinib
indole-hydroxamic
acid
panobinostat,
are
either
under
clinical
evaluations
or
already
been
approved
therapy.
This
indicates
that
rational
design
represents
highly
prospective
approach
development
new
chemotherapeutic
agents.
review
focuses
exploring
therapeutic
delves
into
their
action
mechanisms
well
structure-activity
correlations,
covering
articles
published
between
2021
present.
The
ultimate
goal
offer
foundation
in
future.
An
unprecedented
successive
radical-promoted
thiolative
annulation/Pd-catalyzed
C-H
amination
of
N-benzyl-N-cyanopropiolamides
to
access
pyrrolo[2,1-b]quinazolin-1(9H)-ones
in
a
one-pot
manner
is
described.
Moreover,
altering
the
step
with
oxidation
(reagent
switch)
offered
maleimides
from
same
set
readily
accessible
precursors.
Both
transformations
display
versatility
across
wide
range
substrates,
enabling
efficient
various
functionalized
quinazolin-1-ones
and
good
yields.
Organic Letters,
Год журнала:
2024,
Номер
26(31), С. 6625 - 6630
Опубликована: Авг. 1, 2024
By
employing
elemental
selenium
as
the
source,
we
have
realized
amidine-directed
Rh(III)-catalyzed
cascade
C–H
selenylation/[5
+
1]
annulation
for
direct
construction
of
structurally
novel
selenadiazine,
benzoselenadiazine,
and
benzoselenazol-3-amine
frameworks
with
specific
site
selectivity
good
functional
group
tolerance.
Besides,
obtained
products
can
serve
fundamental
platforms
subsequent
chemical
transformations,
thus,
feasible
SeNEx
reaction,
SeNEx/Michael
addition,
simple
conversion
selenadiazine
product
into
diverse
other
organoselenium
molecules
were
demonstrated
accordingly.
Taken
together,
developed
methodology
efficiently
expands
space
species.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(25), С. 5014 - 5031
Опубликована: Янв. 1, 2024
Transition
metal
catalyzed
C-H
bond
activation
has
become
one
of
the
most
important
tools
for
constructing
new
chemical
bonds.
Introducing
directing
groups
to
substrates
is
key
a
successful
reaction,
these
can
also
be
further
transformed
in
reaction.
Amidines
with
their
unique
structure
and
reactivity
are
ideal
transition
metal-catalyzed
transformations.
This
review
describes
major
advances
mechanistic
investigations
activation/annulation
tandem
reactions
amidines
until
early
2024,
focusing
on
unsaturated
compounds,
such
as
alkynes,
ketone,
vinylene
carbonate,
cyclopropanols
derivatives.
Meanwhile
this
manuscript
explores
reaction
different
carbene
precursors,
example
diazo
azide,
triazoles,
pyriodotriazoles,
sulfoxonium
ylides
well
own
activation/cyclization
reactions.
A
bright
outlook
provided
at
end
manuscript.
Molecules,
Год журнала:
2024,
Номер
29(13), С. 3178 - 3178
Опубликована: Июль 3, 2024
Catalyzed
by
Rh2(esp)2
(10
mol%)
and
(±)-BINAP
(20
in
DCE
at
80
°C,
the
cascade
assembly
between
diazobarbiturates
alkylidene
pyrazolones
proceeded
readily
produced
spiro-furopyrimidines
38–96%
chemical
yields.
The
structure
of
prepared
spirofuro-pyrimidines
was
firmly
confirmed
X-ray
diffraction
analysis.
