Chemical Science,
Год журнала:
2021,
Номер
12(11), С. 4034 - 4040
Опубликована: Янв. 1, 2021
With
the
increasing
awareness
of
sustainable
chemistry
principles,
development
an
efficient
and
mild
strategy
for
C(sp3)-H
bond
activation
nitrogen-containing
compounds
without
utilization
any
oxidant
metal
is
still
highly
desired
challenging.
Herein,
we
present
a
metal-free
reaction
system
that
enables
C-H
functionalization
aliphatic
sulfonamides
using
DABCO
as
promoter
under
conditions,
affording
series
α,β-unsaturated
imines
in
good
yields
with
high
selectivities.
This
protocol
tolerates
broad
range
functionalities
can
serve
powerful
synthetic
tool
late-stage
modification
complex
compounds.
More
importantly,
control
experiments
detailed
DFT
calculations
suggest
this
process
involves
[2
+
2]
cyclization/ring-cleavage
reorganization,
which
opens
up
new
platform
establishment
other
related
reorganization
reactions.
Chemistry - An Asian Journal,
Год журнала:
2020,
Номер
15(8), С. 1225 - 1233
Опубликована: Фев. 27, 2020
The
spirooxindole
unit
is
one
of
the
most
widely
investigated
compound
skeletons
existing
in
numerous
natural
and
pharmaceutical
molecules.
Thus,
a
large
number
synthetic
methodologies
have
already
been
reported
to
construct
such
core
structure.
trifluoromethyl
group
another
privileged
organic
chemistry.
introduction
CF3
an
framework
can
significantly
improve
properties
molecule.
In
this
context,
efficient
approach
for
construction
trifluoromethyl-containing
spirooxindoles
becomes
promising
research
direction
among
communities
industry
academia.
Minireview,
recent
advances
summarized
discussed.
addition,
representative
corresponding
reaction
mechanisms
described
as
well.
European Journal of Organic Chemistry,
Год журнала:
2021,
Номер
2021(11), С. 1653 - 1675
Опубликована: Фев. 23, 2021
Abstract
The
great
variety
of
spirooxindole
three‐dimensional
scaffolds
encompasses
relevant
bioactive
natural
alkaloids
as
well
useful
therapeutic
agents.
In
view
the
challenging
features
skeletons
and
their
desirable
properties,
several
synthetic
routes
have
been
devoted
to
preparation.
Because
both
1,3‐dipolar
species
2‐oxindoles
bearing
a
C=X
double
bond
(X=C<,
N−,
O)
in
3‐position,
prominent
role
relies
upon
cycloaddition
key
step
whole
sequence.
present
paper
aims
discuss
developments
field
synthesis
via
occurred
2011–2020
decade.
literature
data
on
this
subject
are
reviewed
systematic
way
according
type
1,3‐dipole
oxindole
dipolarophile.
Chemistry - An Asian Journal,
Год журнала:
2020,
Номер
15(18), С. 2838 - 2853
Опубликована: Июль 24, 2020
Abstract
Benzothiophene,
benzofuran,
indole,
and
indene
derivatives
are
privileged
heterocyclic
motifs.
These
present
in
a
wide
range
of
bioactive
natural
products
pharmaceutical
drugs
the
subject
materials
science
research.
However,
construction
benzothiophene,
frameworks
have
been
long‐standing
challenges
to
organic
chemists.
In
this
review,
we
classify
four
structures
synthesized
from
2‐benzylidene‐1‐benzofuran‐3‐one
their
analogues
terms
ring
size
(from
three‐
ten‐membered)
type
(fused
or
spiro),
as
well
summarizing
developments
field.
Finally,
discuss
opening
1,4‐addition
reactions.
New Journal of Chemistry,
Год журнала:
2020,
Номер
44(40), С. 17148 - 17176
Опубликована: Янв. 1, 2020
Stereoselective
annulations
of
2-arylidene-1,3-indanediones
towards
spiro-carbocycles
as
well
spiro/fused
heterocycles
based
on
various
cycloadditions
and
tandem
are
described.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(35), С. 7099 - 7104
Опубликована: Янв. 1, 2022
An
efficient
method
to
construct
unique
spiro[indoline-3,4′-pyrrolo[3,4-
b
]pyridines]
was
successfully
developed
via
a
DABCO
promoted
formal
[3
+
3]
cycloaddition
reaction
of
MBH
carbonates
isatins
with
β-enamino
maleimides
under
mild
conditions.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(24), С. 17181 - 17196
Опубликована: Ноя. 28, 2023
A
convenient
synthetic
protocol
for
regioselective
and
diastereoselective
construction
of
complex
dispiro-indanone-fluorenone-oxindole
motifs
was
developed
by
the
base-promoted
annulation
reaction
bindone
MBH
carbonates
isatins
adjusting
conditions.
DABCO
promoted
in
DCM
at
room
temperature,
affording
dispiro[indene-2,4′-fluorene-1′,3″-indoline]
derivatives
good
yields
with
high
diastereoselectivity.
Triethylamine
two
molecular
1,3-indanediones
esters
ethanol
elevated
temperature
selectively
gave
dispiro[indene-2,4′-fluorene-3′,3″-indolines]
moderate
yields.
However,
triethylamine
excess
refluxing
ethanol,
Z-isomer
as
major
product
E-isomer
minor
product.
Organic Chemistry Frontiers,
Год журнала:
2020,
Номер
7(20), С. 3202 - 3208
Опубликована: Янв. 1, 2020
In
the
presence
of
mixed
bases
DABCO
and
K2CO3,
reaction
MBH
maleimides
isatins
with
various
cyclic
1,3-dicarbonyl
compounds
afforded
functionalized
dispiro[indoline-3,3′-furan-2′,3′′-pyrrolidines]
in
satisfactory
yields
high
diastereoselectivity.
Synthesis,
Год журнала:
2021,
Номер
53(21), С. 3869 - 3908
Опубликована: Сен. 2, 2021
This
review
aims
to
provide
a
comprehensive
overview
of
condensation-based
methods
for
the
C-H
bond
functionalization
amines
that
feature
azomethine
ylides
as
key
intermediates.
These
transformations
are
typically
redox-neutral
and
share
common
attributes
with
classic
name
reactions
such
Strecker,
Mannich,
Friedel-Crafts,
Pictet-Spengler,
Kabachnik-Fields
reaction,
while
incorporating
redox-isomerization
step.
approach
provides
an
ideal
platform
rapidly
transform
simple
starting
materials
into
complex
amines.
