Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(24), С. 4427 - 4432
Опубликована: Ноя. 23, 2022
Abstract
A
rhodium‐catalyzed
cascade
cross‐coupling/spirocyclization/formal
[4+2]
cycloaddition
reaction
of
3‐(2‐isocyanoethyl)indoles
with
aromatic
azides
is
developed,
providing
a
general
synthetic
protocol
to
polycyclic
spiroindolines
bearing
pentasubstituted
guanidine
moiety
moderate
excellent
yields.
This
transformation
highly
effective
since
one
C−C,
C=N,
three
C−N
bonds
as
well
two
new
rings
are
constructed
in
single
step.
More
importantly,
this
work
represents
reactivity
pattern
3‐(2‐isocyanoethyl)indole,
and
thus
constitutes
an
valuable
addition
3‐(2‐isocyanoethyl)indole
chemistry.
magnified
image
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(17), С. 4591 - 4597
Опубликована: Янв. 1, 2022
An
asymmetric
cascade
reaction
catalyzed
by
a
chiral
N
,
′-dioxide–Dy(
iii
)
complex
was
realized
to
construct
the
valuable
[6,5,5,6]
tetracyclic
spiroindolines
with
good
yields
and
enantioselectivities
concise
one-step
protocol.
Chemical Communications,
Год журнала:
2023,
Номер
59(43), С. 6576 - 6579
Опубликована: Янв. 1, 2023
An
NBS-induced
intramolecular
annulation
of
3-(1H-indol-3-yl)-N-alkoxypropanamide
is
described.
The
reactions
proceed
well
and
quickly
under
mild
conditions
with
the
help
a
base.
It
was
found
that
C2-substituents
on
indole
ring
in
have
great
influence
upon
reaction.
By
using
C2-methyl-
C2-phenyl-3-(1H-indol-3-yl)-N-alkoxypropanamide
as
templates,
practical
protocols
for
divergent
synthesis
fused-
spirocyclic
indoline
compounds
were
studied
established.
Green Synthesis and Catalysis,
Год журнала:
2022,
Номер
4(2), С. 181 - 185
Опубликована: Июнь 11, 2022
An
annulation
reaction
of
tryptamine-derived
isocyanides
with
hydrazonyl
chlorides
in
the
presence
bases
was
developed.
Controlled
by
different
bases,
[1+
2+3]
and
2+3]/[2
+
3]
cascade
were
realized.
In
latter
reaction,
five
new
chemical
bonds
as
well
three
heterocycles
formed
one
step.
It
showed
extremely
high
efficiency,
relatively
broad
substrate
scope,
milder
conditions,
good
tolerance
functional
groups
chemoselectivity.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(24), С. 4427 - 4432
Опубликована: Ноя. 23, 2022
Abstract
A
rhodium‐catalyzed
cascade
cross‐coupling/spirocyclization/formal
[4+2]
cycloaddition
reaction
of
3‐(2‐isocyanoethyl)indoles
with
aromatic
azides
is
developed,
providing
a
general
synthetic
protocol
to
polycyclic
spiroindolines
bearing
pentasubstituted
guanidine
moiety
moderate
excellent
yields.
This
transformation
highly
effective
since
one
C−C,
C=N,
three
C−N
bonds
as
well
two
new
rings
are
constructed
in
single
step.
More
importantly,
this
work
represents
reactivity
pattern
3‐(2‐isocyanoethyl)indole,
and
thus
constitutes
an
valuable
addition
3‐(2‐isocyanoethyl)indole
chemistry.
magnified
image
