Abstract
Indole
derivatives
substituted
at
the
C‐2
position
have
shown
important
biological
activities.
Due
to
these
properties,
several
methods
been
described
for
preparation
of
structurally
diverse
indoles.
In
this
work,
we
synthesized
highly
functionalized
indole
via
Rh(III)‐catalyzed
alkylation
with
nitroolefins.
Under
optimized
condition,
23
examples
were
prepared
39–80
%
yield.
Moreover,
nitro
compounds
reduced
and
submitted
Ugi
four‐component
reaction,
furnishing
a
series
new
indole‐peptidomimetics
in
moderate
good
overall
yields.
Chemical Communications,
Год журнала:
2024,
Номер
60(34), С. 4613 - 4616
Опубликована: Янв. 1, 2024
We
report
an
innovative
synthetic
strategy
for
the
generation
of
polysubstituted
indoles
from
indolines,
aryldiazonium
salts,
and
azoles.
The
methodology
encompasses
electrophilic
substitution
reaction
affording
C5-indoline
intermediates
which
undergo
iodine-mediated
oxidative
transformation
coupled
with
C-H
functionalization
to
yield
indole
derivatives.
Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(8)
Опубликована: Июнь 21, 2023
Abstract
Indole
heterocycles
hold
an
important
position
in
chemical
landscape
because
of
their
prominence
natural
products
and
pharmaceuticals.
Consequently,
development
new
efficient
strategies
to
access
indole
scaffold
are
continuous
interest.
For
the
past
few
years,
gold‐catalyzed
activation
alkyne
has
emerged
as
a
powerful
strategy
for
constructing
heterocyclic
skeleton.
The
present
review
highlights
recent
advances
(2018–2023)
toward
synthesis
skeletons
via
annulations
alkynes.
A
variety
alkynes,
such
as,
ynamides,
azido
ortho
‐alkynyl
anilines,
propargylic
alcohols,
phenylimines,
miscellaneous
alkynes
employed
affording
various
architectures
under
gold
catalysis.
Moreover,
mechanisms
included
most
cases
better
understanding
reaction
pathway.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(9), С. 2607 - 2612
Опубликована: Янв. 1, 2024
A
metal-free,
scalable,
and
cascade
protocol
for
assembling
diverse
polysubstituted
pyridines
from
tertiary
enaminones
α,β-unsaturated
sulfonylketimines
by
cleaving
C–N/N–S
bonds
is
reported.
ACS Omega,
Год журнала:
2023,
Номер
8(31), С. 27894 - 27919
Опубликована: Июль 25, 2023
Polycyclic
fused
indoles
are
ubiquitous
in
natural
products
and
pharmaceuticals
due
to
their
immense
structural
diversity
biological
inference,
making
them
suitable
for
charting
broader
chemical
space.
Indole-based
polycycles
continue
be
fascinating
as
well
challenging
targets
synthetic
fabrication
because
of
characteristic
frameworks
possessing
biologically
intriguing
compounds
both
origin.
As
a
result,
an
assortment
new
processes
catalytic
routes
has
been
established
provide
unified
access
these
skeletons
very
efficient
selective
manner.
Transition-metal-catalyzed
processes,
particular
from
rhodium(III),
widely
used
endeavors
increase
molecular
complexity
efficiently.
In
recent
years,
this
resulted
significant
progress
reaching
scaffolds
with
enormous
activity
based
on
core
indole
skeletons.
Additionally,
Rh(III)-catalyzed
direct
C–H
functionalization
benzannulation
protocols
moieties
were
one
the
most
alluring
techniques
generate
indole-fused
polycyclic
molecules
This
review
sheds
light
developments
toward
synthesizing
by
cascade
annulation
methods
using
Rh(III)-[RhCp*Cl2]2-catalyzed
pathways,
which
align
comprehensive
sophisticated
field
functionalization.
Here,
we
looked
at
few
cascade-based
designs
catalyzed
Rh(III)
that
produced
elaborate
inspired
bioactivity.
The
also
strongly
emphasizes
mechanistic
insights
1–2,
2–3,
3–4-fused
systems,
focusing
routes.
With
emphasis
efficiency
product
diversity,
chosen
carbocycles
heterocycles
least
three
fused,
bridged,
or
spiro
cages
reviewed.
newly
created
synthesis
concepts
toolkits
accessing
diazepine,
indol-ones,
carbazoles,
benzo-indoles,
illustrative
privileged
techniques,
included
featured
collection.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(14), С. 10272 - 10282
Опубликована: Июль 5, 2024
The
exploration
of
remote
functionalization
indoles
is
impeded
by
the
inherently
dominant
reactivity
intrinsic
to
pyrrole
moiety.
Herein,
we
delineate
a
novel
strategy
facilitated
Lewis
acid
mediation,
enabling
C-H
functionalization,
which
culminates
in
synthesis
an
array
selectively
functionalized
indole
derivatives,
encompassing
3-trifluoroacetyl
and
5-benzoyl
motifs,
utilizing
trifluoroacetic
anhydride
various
acyl
chlorides.
Notably,
protocol
exhibits
versatility,
as
epitomized
extension
C5-acylation
alkylation
sulfonation
reactions.
This
methodology
distinguished
its
exemplary
regio-
chemo-selectivity,
extensive
substrate
scope,
commendable
tolerance
diverse
functional
groups,
employment
comparatively
mild
reaction
conditions.
Green Chemistry,
Год журнала:
2023,
Номер
26(4), С. 1990 - 1999
Опубликована: Дек. 21, 2023
A
highly
“green”
and
efficient
method
to
furnish
biologically
important
3,3′,3′′-trisindoles
via
a
graphene
oxide-catalysed
carbene-transfer
reaction
of
3-diazo
oxindole
as
carbene
precursor
with
indoles
is
described.
Organic Letters,
Год журнала:
2023,
Номер
25(17), С. 3034 - 3039
Опубликована: Апрель 24, 2023
A
catalyst-controlled
divergent
synthesis
of
bridged
[3.3.1]
bis(indolyl)-oxanes
and
cis-[6.7]
fused
bis(indolyl)
oxepanes
via
diastereoselective
desymmetrization
bis(indolyl)-cyclohexadienones
is
presented
for
the
first
time.
The
reaction
highly
atom-
step-economic,
furnishing
sp3-rich
functionalized
derivatives
in
good
to
excellent
yields
with
wide
substrate
scope.
proceeds
through
Friedel-Crafts
alkylation
followed
by
selective
C-C
bond
formation/rearrangement.
Gram
scale
synthetic
utility
generate
alkaloid-like
molecular
diversity
were
also
illustrated.
Abstract
Herein,
we
report
the
selective
synthesis
of
3‐hydroxy
bisindoles
via
an
engineered
myoglobin‐catalyzed
Friedel–Crafts
reaction
isatin
and
indole.
Initially,
was
carried
out
using
wild‐type
myoglobin
as
a
catalyst,
but
conversion
low.
Therefore,
library
Mb‐variants
generated
utilizing
site‐directed
mutagenesis
technique
obtained
double‐mutated
Mb(H64V,
V68A)
variant
highly
reactive
biocatalyst
for
this
transformation.
Additionally,
robustness
generality
protocol
have
been
demonstrated
by
setting
up
scale‐up
reactions
variously
substituted
isatins
indoles
which
produce
desired
in
66–93
%
isolated
yield.
Next,
enzymatic
approach
combined
with
carbocatalytic
graphene
oxide
catalyst
to
generate
C‐3
sulfenylated
bisindole
derivatives
one‐pot
manner.
