ChemistrySelect,
Journal Year:
2022,
Volume and Issue:
7(11)
Published: March 16, 2022
Abstract
Indium‐mediated
allylation
of
N
‐
tert
‐butanesulfinyl
imines
derived
from
indole‐2
and
3‐carbaldehydes
3
5
with
allylic
bromides
6
,
proceed
high
diastereoselectivity.
Homoallylic
amide
derivatives
13
14
are
transformed
into
dihydropyridinones
15
16
upon
successive
desulfinylation,
‐acylation
acryloyl
chloride
ring‐closing‐metathesis.
Desulfinylation
amine
ester
17
18
obtained
when
ethyl
2‐(bromomethyl)acrylate
(
b
)
is
used
as
the
allylating
reagent,
lead
to
corresponding
α‐methylene‐γ‐butyrolactams
19
20
in
modest
yields.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
10(2), P. 540 - 547
Published: Dec. 10, 2022
An
efficient
synthetic
protocol
for
the
selective
construction
of
spiro[indoline-3,5′-pyrrolo[3,4-
b
]azepines]
and
spiro[indoline-3,3′-pyrroles]
via
a
cycloaddition
reaction
α,β-unsaturated
aldimines
MBH
adducts
isatins
was
successfully
developed.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(9), P. 5440 - 5456
Published: April 3, 2023
p-TsOH-catalyzed
cycloaddition
of
various
3-vinylindoles
and
(indol-2-yl)diphenylmethanols
in
acetonitrile
gave
the
functionalized
cyclopenta[b]indoles
good
yields
with
high
diastereoselectivity
via
[3
+
2]
reaction.
More
importantly,
FeCl3-catalyzed
annulation
reaction
afforded
unexpected
cyclohepta[1,2-b:4,5-b']diindoles
satisfactory
yields,
which
a
formal
[4
3]
an
unprecedented
C3/C2
carbocation
rearrangement
were
first
confirmed
by
determination
single-crystal
structure.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(21), P. 8365 - 8369
Published: Oct. 15, 2021
A
rhodium-catalyzed
diastereoselective
formal
[5
+
2]
annulation
of
indoles
with
cyclohexadienone-containing
1,6-enynes
has
been
established
via
indole
2,3-difunctionalization.
The
reaction,
probably
proceeding
through
tandem
C2–H
alkenylation
and
intramolecular
Friedel–Crafts
alkylation
relay,
provides
rapid
construction
indole-fused
oxepines
in
good
to
excellent
yields
a
broad
substrate
scope.
This
method
also
features
concomitant
cis-hydrobenzo[b]
oxepine
scaffolds,
core
unit
found
numerous
natural
products
important
biological
activities.
New Journal of Chemistry,
Journal Year:
2023,
Volume and Issue:
47(14), P. 6694 - 6699
Published: Jan. 1, 2023
The
polycyclic
cyclohepta[
b
]indoles
were
efficiently
obtained
via
a
formal
[4+3]
cycloaddition
and
an
unprecedented
rearrangement
of
the
maleimide
motif
from
C3/C2-position
indole
ring.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(8), P. 1299 - 1304
Published: Feb. 21, 2023
The
unique
reactivity
of
in
situ
generated
propargylic
para-quinone
methides
as
a
new
type
five-carbon
synthon
has
been
discovered
by
novel
bismuth(III)-catalyzed
tandem
annulation
reaction.
This
1,8-addition/cyclization/rearrangement
cyclization
cascade
reaction
is
characterized
unusual
structural
reconstruction
2-vinylphenol,
involving
cleavage
the
C1'═C2'
bond
and
formation
four
bonds.
method
provides
convenient
mild
approach
to
generate
synthetically
important
functionalized
indeno[2,1-c]chromenes.
mechanism
proposed
from
several
control
experiments.
Beilstein Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
19, P. 1923 - 1932
Published: Dec. 18, 2023
A
straightforward
synthetic
protocol
for
the
efficient
construction
of
diazepine-containing
spiroindolines
has
been
developed
and
proceeds
through
a
by
base-promoted
annulation
reaction
α-halogenated
N
-acylhydrazones
isatin-derived
MBH
carbonates.
The
mechanism
this
formal
[4
+
3]
includes
in
situ
generated
allylic
ylide,
nucleophilic
substitution,
Michael
additon,
elimination
processes.
Additionally,
similar
with
-tosylhydrazones
also
afforded
-tosyl-substituted
spiro[indoline-3,5'-[1,2]diazepine]
satisfactory
yields.
This
provides
convenient
approach
assembly
diverse
highly
functionalized
spiro[indoline-3,5'-[1,2]diazepines]
features
broad
substrate
scope,
simple
conditions,
high
molecular
convergence.
