The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(17), P. 12128 - 12142
Published: Aug. 22, 2024
We
herein
reveal
a
streamlined
synthesis
of
structurally
fused
6-iminoisoindoloindolones
via
meticulously
orchestrated
cascade
reaction.
This
process
seamlessly
intertwines
2-alkynylaniline
and
2-formylbenzonitrile
under
the
catalytic
influence
TMSOTf,
giving
rise
to
these
compounds
in
remarkable
yields
that
stand
as
testament
efficiency
our
approach.
Moreover,
versatility
this
synthetic
strategy
extends
far
beyond
mere
synthesis,
offering
gateway
creation
both
isoindoloindolone
unprecedented
diphenylbenzopyrrolizinoisoquinolinone
derivatives,
thereby
opening
new
horizons
realm
chemical
innovation.
Furthermore,
strategic
elegance
methodology
is
underscored
by
its
potential
for
scale-up
production
applicability
across
diverse
contexts.
Chemical Reviews,
Journal Year:
2024,
Volume and Issue:
124(12), P. 7907 - 7975
Published: May 29, 2024
The
increasing
importance
of
azaheterocyclic
phosphonates
in
the
agrochemical,
synthetic,
and
medicinal
field
has
provoked
an
intense
search
development
synthetic
routes
for
obtaining
novel
members
this
family
compounds.
This
updated
review
covers
methodologies
established
since
2004,
focusing
on
synthesis
phosphonates,
which
phosphonate
moiety
is
directly
substituted
onto
to
structure.
Emphasizing
recent
advances,
classifies
newly
developed
approaches
according
ring
size
providing
information
biological
activities
whenever
available.
Furthermore,
summarizes
various
methods
formation
C–P
bonds,
examining
sustainable
such
as
Michaelis–Arbuzov
reaction,
Michaelis–Becker
Pudovik
Hirao
coupling,
Kabachnik–Fields
reaction.
After
analyzing
applications
investigated
years,
a
predominant
focus
evaluation
these
compounds
anticancer
agents
evident.
emerging
underline
versatility
potential
compounds,
highlighting
need
continued
research
expand
interesting
family.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(10)
Published: Jan. 9, 2024
Abstract
We
present
the
first
example
of
electrocatalytic
three‐component
annulation–iodosulfonylation
indole‐tethered
1,6‐enynes
with
arylsulfonyl
hydrazides
and
KI
for
accessing
various
iodosulfonated
pyrrolo[1,2‐
a
]indoles
in
moderate
to
excellent
yields
high
stereospecificity.
This
electrosynthesis
opens
new
avenues
construction
skeleton
good
functional
group
compatibility
under
environmentally
benign
condition.
Based
on
control
experiments
cyclic
voltammetry
data,
we
suggested
plausible
reaction
mechanism
which
included
anodic
oxidation,
homolysis
iodide,
radical
addition,
5
‐
exo
dig
cyclization,
coupling
or
nucleophilic
attack
iodide
ions
cascade.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(5), P. 1213 - 1218
Published: Feb. 2, 2022
A
mild
visible-light-driven
palladium-catalyzed
radical
tandem
dearomatization
of
indoles
with
unactivated
alkenes
is
described
moderate
to
good
yields
and
excellent
diastereoselectivities.
Under
visible-light
irradiation,
the
photoexcited
state
palladium
complex
was
formed,
which
could
transfer
a
single
electron
N-(2-bromobenzoyl)indoles,
leading
hybrid
chemistry.
This
provides
efficient
atom-economical
access
diverse
2,3-disubstituted
indoline
derivatives.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(22), P. 4583 - 4588
Published: Feb. 11, 2024
The
iron-mediated
hydrogen
atom
transfer
(HAT)
reaction
is
efficaciously
employed
for
the
synthesis
of
dihydropyrroloindoles
and
dihydropyrrolizines
via
5-exo-trig
radical
cyclization
where
indoles
pyrroles
are
used
as
an
acceptor.
This
approach
has
also
been
extended
tetrahydrocyclopenta[b]indolones
Baldwin-disfavored
5-endo-trig
pathway.
formal
bruceolline
J
total
bruceollines
E
H
have
expeditiously
carried
out
by
employing
former
strategy.
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(19)
Published: Jan. 2, 2024
Novel
rhodium-catalyzed
[3+3]
annulations
of
diazoenals
and
α-amino
ketones
has
been
disclosed
here.
The
reactivity
switched
from
carbenoid
to
vinylogous
NH-insertion
by
altering
acyclic
cyclic
ketones.
In
this
direction,
we
report
an
efficient
strategy
synthesize
1,2-dihydropyridines
(DHPs)
fused
1,4-oxazines.
Mechanistic
investigation
revealed
that
the
formyl
group
is
necessary
for
annulation
cyclohexyl
dictating
factor
NH-
insertion.
synthetic
utility
was
demonstrated
synthesizing
piperidine,
pyrido[1,2-a]indole,
2-pyridone
scaffolds.
Further,
structural
diversification
1,4-oxazines
resulted
in
short
synthesis
hexahydroquinolin-2(1H)-ones,
hexahydro
quinolines
tetrahydroquinolinones
via
ring
opening
rearrangement
a
new
oxidative
deformylation,
respectively.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(4), P. 909 - 913
Published: Jan. 11, 2022
Abstract
A
palladium‐catalyzed
stereoselective
intramolecular
Heck
dearomative
of
indoles
with
silyl
termination
has
been
developed.
type
tetracyclic
indoline
derivatives
containing
silicon
were
prepared,
involving
N
‐(2‐bromobenzoyl)indoles
and
silylboronates.
This
protocol
not
only
led
to
a
broad
substrate
scope
in
acceptable
yields
but
also
could
be
scaled
up
gram
quantities
as
well
further
synthetic
transformation.
magnified
image
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(11), P. 7552 - 7560
Published: May 28, 2024
Herein,
a
palladium-catalyzed
diastereoselective
dearomatization/cross-coupling
cyclization
reaction
between
N-arylacyl
indoles
and
(E)-β-chlorovinyl
ketones
is
reported.
Through
this
cyclization/cycloisomerization
cascade,
series
of
furan-containing
indolines
were
obtained
in
yields
up
to
95%.
The
features
readily
accessible
starting
materials,
benzyl
Pd(II)-catalyzed
cycloisomerization
ketones,
the
sequential
formation
three
bonds
bis-heterocycles,
excellent
diastereoselectivity.
More
importantly,
carbene–secondary
migratory
insertion
proven
be
critical
process
cyclizations.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(17), P. 3578 - 3584
Published: June 18, 2024
Abstract
A
copper‐catalyzed
radical‐induced
annulation‐halocyanomethylation
of
indole‐linked
1,6‐enynes
has
been
established
using
haloacetonitrile
as
radical
precursors,
enabling
the
synthesis
21
cyanomethylated
pyrrolo[1,2‐
a
]indoles
with
yields
ranging
from
42%
to
81%
and
Z
/
E
ratio
up
19:1.
Moreover,
by
adjusting
reaction
temperature,
variation
annulation‐bromobicyanomethylation
process
was
achieved,
resulting
in
production
12
bicyanomethylated
]indole
isomers
41–68%.
The
stereoisomeric
mixture
products
could
be
purified
their
pure
configurations
through
recrystallization.
proposed
mechanism
formulated
series
control
experiments.
