Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(24), P. 4427 - 4432
Published: Nov. 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,
Journal Year:
2023,
Volume and Issue:
10(7), P. 1660 - 1668
Published: Jan. 1, 2023
An
efficient
Mn(
iii
)-promoted
cascade
reaction
of
tryptamine-derived
isocyanides
with
arylboronic
acids
for
accessing
spiroindoline
derivatives
is
described.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(4), P. 2247 - 2263
Published: Feb. 7, 2024
A
simple
and
atom
economic
protocol
for
the
construction
of
C–X/C–C
bonds
via
catalytic
aminium
radical-cation
salt
(Magic
Blue)-initiated
SN2-type
nucleophilic
ring-opening
transformations
racemic
nonracemic
aziridines
with
different
hetero
carbon
nucleophiles
to
afford
various
amino
ethers,
thioethers,
amines
in
up
99%
yield,
perfect
enantiospecificity
some
substrates
but
reduced
ee
others
(for
aziridines),
is
developed.
This
salt-initiated,
strategy,
along
cyclization
protocols,
employed
synthesize
biologically
significant
compounds.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
27(4), P. 989 - 994
Published: Jan. 21, 2025
Herein,
we
report
an
electricity-driven
activation
of
aziridine
via
direct
anodic
oxidation
to
give
N-heterocycles
and
1,2-bifunctionalized
products
by
excluding
any
oxidant/reductant
or
metal
catalyst.
Many
structurally
modified
aziridines
were
employed
in
the
presence
different
nitriles.
A
large
variety
nucleophiles
screened
furnish
chemoselectively
O-alkylated
C-alkylated
products.
Late-stage
derivatization
with
natural
medicinally
active
compounds
has
also
been
done.
Remarkably,
our
strategy
was
found
be
a
greener,
sustainable,
atom-economical
approach
(E-factor
=
ca.
0.8).
Azetidine
compatible
protocol
generated
six-membered
N-heterocycles.
The
detailed
mechanistic
study
highlighted
that
reaction
is
driven
generation
radical
cation
followed
SN2
nucleophilic
attack.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(21), P. 3829 - 3834
Published: May 17, 2023
Magnesium(II)-catalyzed
cascade
reactions
of
N,N'-cyclic
azomethine
imines
with
indolyl-substituted
isocyanides
are
reported
herein.
The
method
exhibited
a
high
functional
group
tolerance
and
broad
substrate
scope.
A
series
anti-pentacyclic
spiroindolines
containing
N,N'-fused
heterocycle
skeletons
were
obtained
in
up
to
82%
yield
8.5:1
dr
under
mild
reaction
conditions.
Intriguingly,
sequential
HOAc-mediated
protonation
results
diastereoenriched
epimerization,
which
gives
rise
the
syn-pentacyclic
as
sole
isomers.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(37), P. 6700 - 6704
Published: Sept. 12, 2022
A
dearomative
spirocyclization
of
tryptamine-derived
isocyanides
with
quinone
esters
is
developed
for
the
divergent
synthesis
structurally
complex
chromeno[2,3-b]indole
and
polycyclic
spiroindoline
scaffolds.
This
domino
reaction
features
formation
conversion
six-membered
dihydropyran
ring
an
amendable
N,O-aminal
moiety.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(55), P. 8572 - 8575
Published: Jan. 1, 2023
A
new
type
of
metal-free
[5+1]
cycloaddition
reaction
donor-acceptor
aziridines
with
2-(2-isocyanoethyl)indoles
is
reported
herein.
This
method
exhibits
broad
substrate
scope
and
atom-economy.
series
2H-1,4-oxazines
containing
an
indole
heterocycle
skeleton
were
obtained
in
up
to
92%
yield
under
mild
conditions.
Control
experiments
revealed
that
free
N-H
crucial
for
the
above
transformations.
The
theoretical
calculation
studies
provided
guidance
on
in-depth
insight
into
mechanism
hydrogen-bond
between
carbonyl
group
was
identified
lower
energy
barrier
transition
states.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(13), P. 9543 - 9553
Published: June 12, 2023
A
catalyst-free
cascade
reaction
of
3-(2-isocyanoethyl)indoles
and
1-sulfonyl-1,2,3-triazoles
was
realized.
This
dearomative
spirocyclization
provided
an
efficient
protocol
to
synthesize
a
series
polycyclic
indolines
bearing
spiro-α-carboline
in
moderate
high
yields
one
step
under
thermal
conditions.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(24), P. 17345 - 17355
Published: Dec. 4, 2023
Tryptamine-derived
isocyanides
are
valuable
building
blocks
in
the
construction
of
spirocyclic
indolenines
and
indolines
via
dearomatization
indole
moiety.
We
report
Bu4N[Fe(CO)3NO]-catalyzed
carbene
transfer
α-diazo
esters
to
3-(2-isocyanoethyl)indoles,
leading
ketenimine
intermediates
that
undergo
spontaneous
dearomative
spirocyclization.
The
utility
this
iron-catalyzed
transfer/spirocyclization
cascade
was
demonstrated
by
its
use
as
a
key
step
formal
total
synthesis
monoterpenoid
alkaloids
(±)-aspidofractinine,
(±)-limaspermidine,
(±)-aspidospermidine,
(±)-17-demethoxy-N-acetylcylindrocarine.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(15), P. 3303 - 3309
Published: June 15, 2024
Abstract
We
herein
reported,
a
visible‐light‐induced
K
2
S
O
8
mediated
cascade
reaction
of
3‐(2‐isocyanoethyl)indoles
with
α
‐oxocarboxylic
acids
leading
to
diastereoselective
synthesis
polycyclic
spiroindolines
bearing
an
N
‐formyl
unit
derivative
utilising
the
alkali
metal
salt
as
mediator
under
mild
conditions.
This
study
offers
illustration
and
3‐(2‐isocyanoethyl)indoles‐based
reactions
it
shows
involvement
glyoxolate
ions
without
decarboxylation
access
analogue.
The
batch
process
can
be
extended
continuous
flow
system
using
glass
tube
loaded
placed
between
PFA
capillary
reactor,
which
greatly
advance
efficiency
even
promoted
gram‐scale
synthesis.
