Chemical Communications,
Год журнала:
2023,
Номер
59(31), С. 4652 - 4655
Опубликована: Янв. 1, 2023
Herein,
previously
unreported
Fischer's
base
reactants
serving
as
useful
2C
building
blocks
in
(3+2)
cycloaddition
reactions
to
build
a
library
of
bispiro[Fischer's
base-oxindole]
hybrids
are
described.
These
structurally
intriguing
products
containing
three
adjacent
quaternary
stereocentres
were
smoothly
afforded
up
82%
yield
and
>20
:
1
dr
under
catalyst-free
conditions.
Notably,
the
present
protocol
firstly
employs
3-isothiocyanato
oxindole
an
acceptor
then
donor
formal
cycloadditions,
allowing
practical,
straightforward
access
diverse
cycloadducts.
This
work
expands
applicability
scope
oxindoles,
which
have
been
limited
behaving
donor/acceptor-based
synthons
cycloadditions
previous
work.
Chemical Reviews,
Год журнала:
2024,
Номер
124(3), С. 1122 - 1246
Опубликована: Янв. 2, 2024
Dearomatization
reactions
have
become
fundamental
chemical
transformations
in
organic
synthesis
since
they
allow
for
the
generation
of
three-dimensional
complexity
from
two-dimensional
precursors,
bridging
arene
feedstocks
with
alicyclic
structures.
When
those
processes
are
applied
to
pyridines,
quinolines,
and
isoquinolines,
partially
or
fully
saturated
nitrogen
heterocycles
formed,
which
among
most
significant
structural
components
pharmaceuticals
natural
products.
The
inherent
challenge
lies
low
reactivity
heteroaromatic
substrates,
makes
dearomatization
process
thermodynamically
unfavorable.
Usually,
connecting
event
irreversible
formation
a
strong
C–C,
C–H,
C–heteroatom
bond
compensates
energy
required
disrupt
aromaticity.
This
aromaticity
breakup
normally
results
1,2-
1,4-functionalization
heterocycle.
Moreover,
combination
these
subsequent
tandem
stepwise
protocols
allows
multiple
heterocycle
functionalizations,
giving
access
complex
molecular
skeletons.
aim
this
review,
covers
period
2016
2022,
is
update
state
art
nucleophilic
dearomatizations
showing
extraordinary
ability
dearomative
methodology
indicating
their
limitations
future
trends.
Organic Letters,
Год журнала:
2022,
Номер
24(10), С. 2008 - 2013
Опубликована: Март 10, 2022
We
report
an
unexpected
dearomative
periphery
modification
strategy
for
transforming
quinolinium
salts
into
structurally
crowded
pyrrolidine–tetrahydroquinoline
polycyclic
systems
with
complete
regio-
and
diastereoselectivity.
Importantly,
the
reaction
pathway
was
regulated
by
simply
tuning
substituents,
achieving
substituent-directed
divergent
synthesis.
The
notable
features
of
this
transformation
include
readily
available
starting
materials,
green
conditions,
a
simple
workup
procedure,
high
bond-
ring-forming
efficiency,
diverse
Synthesis,
Год журнала:
2023,
Номер
56(01), С. 55 - 70
Опубликована: Янв. 17, 2023
Abstract
Despite
its
challenges,
the
skeletal
editing
of
mono-azaarenes
(pyridines,
quinolines,
and
isoquinolines)
has
shown
unparalleled
synthetic
utility
in
construction
complex
molecules
that
are
difficult
to
access
by
conventional
methods.
In
this
short
review,
we
summarize
three
most
recently
developed
strategies
for
deconstruction
azaarene
cores,
with
a
focus
on
their
generality,
limitations,
mechanistic
aspects.
Also,
application
strategy
total
synthesis
some
important
natural
products
is
discussed.
1
Introduction
2
Skeletal
Editing
Mono-Azaarenes
through
Zincke-like
Reactions
3
Mono-azaarenes
Aza-Buchner
4
via
Photoinduced
Radical
or
Energy-Transfer
Processes
5
Conclusion
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(13), С. 3307 - 3312
Опубликована: Янв. 1, 2023
An
unprecedented
example
of
skeletal
editing
pyrrolidines
to
1,2-oxazinanes
expands
the
applicability
scope
“single-atom”
skeletal-editing
technologies.
RSC Advances,
Год журнала:
2022,
Номер
12(38), С. 24681 - 24712
Опубликована: Янв. 1, 2022
The
current
study
highlighted
the
significance
of
β-aminoketones
as
privileged
biologically
active
molecules,
recent
synthetic
strategies,
and
applications.
Chemical Science,
Год журнала:
2022,
Номер
14(3), С. 485 - 490
Опубликована: Дек. 21, 2022
We
report
conjugated
methine
compounds
generated
from
N
-arylpyridiniums
and
amines;
streptocyanines
can
be
used
as
a
new
activation
mode
for
amine
catalysis
applied
to
the
conversion
of
pyridine
rings
benzene
rings.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2538 - 2549
Опубликована: Фев. 1, 2024
A
facile
and
convenient
protocol
for
the
regioselective
construction
of
functionalized
2-hydroxybenzophenones
is
described.
This
involves
Sc(OTf)3/BF3·OEt2-catalyzed
benzannulation
2-vinyloxirans
with
3-formylchromone,
which
cascade
in
situ
diene
formation,
[4
+
2]
cycloaddition,
elimination,
ring-opening
strategies.
Moreover,
it
provides
an
expedited
synthetic
pathway
to
access
biologically
intriguing
1,4-naphthoquinones
anthraquinones
including
vitamin
K3
tectoquinone.
The
synthesized
compounds
also
hold
potential
use
as
UV
filters
show
promise
chemosensors
Cu2+
Mg2+
ions.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(23), С. 4681 - 4698
Опубликована: Янв. 1, 2022
Salicyloylbenzene/heterocycles
are
privileged
scaffolds
found
in
many
natural
products
and
bioactive
molecules.
Numerous
useful
approaches
for
the
preparation
of
these
have
been
developed
recent
years.
Among
approaches,
chromone-based
reactants
demonstrated
their
importance
synthesis
salicyloylbenzene/heterocycle
with
structural
complexity
potential
biological
appeal.
In
this
review,
advances
salicyloylbenzene/heterocycles
summarized
discussed
according
to
which
could
be
achieved
one
step
via
ring-opening
skeletal
reconstruction
reactions.
Both
mechanisms
applications
corresponding
organic
medicinal
chemistry
also
described.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(5), С. 2809 - 2821
Опубликована: Фев. 9, 2023
A
facile
route
for
direct
access
to
the
4-iodopyrrole-2-carbaldehydes
from
pyridinium
salts
has
been
successfully
developed,
which
undergoes
cascade
pyrrole-2-carbaldehydes
construction/selective
C4
position
iodination
process.
Using
Na2S2O8
as
an
oxidant
and
readily
available
sodium
iodide
iodine
source,
a
variety
of
were
obtained
in
good
excellent
yields.
Atom-
step-economy,
functional
group
tolerance,
high
regioselectivity,
well
mild
conditions
entail
this
transformation
alternative
strategy
enriching
pyrroles
library.
Organic Letters,
Год журнала:
2022,
Номер
24(16), С. 3048 - 3052
Опубликована: Апрель 15, 2022
Herein,
we
present
a
new
annulation
reaction
of
quinolinium
salts
with
indoles
and
paraformaldehyde,
which
enables
syn-diastereoselective
construction
vast
range
fused
tetrahydroquinolines
via
ruthenium-catalyzed
hydride-transfer-initiated
tandem
functionalization
the
quinoline
skeleton.
The
developed
transformation
proceeds
mild
conditions,
good
substrate
functional
group
compatibility,
readily
available
feedstocks,
operational
simplicity.
