One-Step Synthesis of Indoloquinoline Alkaloids via the Pd-Catalyzed Larock/Ligand-Accelerated C–H Activation Cascade Reaction
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 16, 2025
Pd-catalyzed
cascade
annulation
of
2-iodoanilines
with
N,3-diphenylpropiolamides
was
achieved,
which
afforded
a
series
indolo[2,3-c]quinolinones
good
yields
and
functional
group
compatibility.
Previously,
the
retro-synthetic
routine
for
indolo[2,3-c]quinolinone
skeleton
has
often
involved
intramolecular
disconnection
C(sp2)-C(sp2)
bond
at
variable
positions,
necessitates
construction
an
indole
or
quinoline
reactant
multiple
pre-set
functionalities.
Meanwhile,
using
C-H
activation
strategy
to
construct
indoloquinoline
is
limited
cases
in
must
be
bearing
nonremovable
directing
group.
Therefore,
circumvent
these
limitations,
we
herein
report
Larock/ligand-accelerated
one-pot
fashion.
This
transformation
2-amidoindole
relies
on
Larock
reaction,
then
forms
C-N
afford
via
ligand-enabled
activation.
Язык: Английский
Synthesis of γ‐ and β‐Carbolines via Diphenyl Phosphate‐Mediated Condensation of 3/2‐Carbonyl‐2/3‐Vinylindoles with Phenyl Hydrazine Followed by Electrocyclization
ChemistrySelect,
Год журнала:
2024,
Номер
9(46)
Опубликована: Дек. 1, 2024
Abstract
A
facile
synthesis
of
3‐alkyl‐2‐aryl
substituted
γ‐carboline
derivatives
is
reported
involving
diphenyl
phosphate
catalyzed
condensation
3‐(acetyl/propionyl)‐2‐(nitroaryl)vinyl‐1‐phenylsulfonylindoles
with
phenyl
hydrazine
followed
by
concurrent
electrocyclization
and
aromatization
through
elimination
aniline.
This
strategy
could
be
successfully
explored
1‐phenylsulfonylindole‐3/2‐carboxaldehydes
containing
vinyl
unit
at
2/3‐position
to
afford
the
respective
γ‐and
β‐carboline
derivatives.
The
domino
reaction
easily
accessible
2/3‐carbonyl
indoles
a
adjacent
positions
as
an
amine
source
afforded
wide
variety
carboline
in
good
acceptable
yields.
synthetic
utility
representative
demonstrated
via
transformation
into
corresponding
indolo[a]carboline
framework.
Язык: Английский