European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
unknown
Published: Sept. 13, 2023
Abstract
Quinobenzazepines
are
useful
in
medicinal
chemistry,
but
their
synthesis
is
very
challenging.
Herein,
we
designed
and
synthesized
a
range
of
multi‐functional
chalcone‐based
quinolinium
salts;
synthetic
application
the
rapid
straightforward
construction
quinobenzazepines
was
successfully
explored.
A
wide
oxa‐bridged
quinobenzazepine
polycycles
were
afforded
serendipitously
through
dearomative
cascade
reaction
our
newly
developed
salts
acetylacetone.
This
strategy
features
high
bond‐
ring‐forming
efficiency
complete
regio‐
diastereoselective
control.
Synthesis,
Journal Year:
2023,
Volume and Issue:
56(01), P. 55 - 70
Published: Jan. 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
Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(57), P. 7964 - 7967
Published: Jan. 1, 2022
An
interrupted
dearomative
reduction
strategy
was
developed
to
transform
planar
chalcone-based
pyridinium
salts
into
structurally
intriguing
bridged
piperidines
in
a
completely
regio-
and
diastereoselective
manner.
This
reaction
proceeded
successfully
by
using
cheap
easily
accessible
NaBH4
as
the
reductant
under
mild
conditions
without
exclusion
of
oxygen
or
use
special
equipment.
Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(61), P. 8576 - 8579
Published: Jan. 1, 2022
Herein,
we
report
a
substrate-directed
diverse
synthetic
strategy
toward
two
kinds
of
structurally
intriguing
fused
indole
polycycles
through
Rh(
ii
)-catalyzed
cascade
reactions
bis(diazo)indolin-2-ones
with
enaminones.
Molecular Catalysis,
Journal Year:
2024,
Volume and Issue:
559, P. 114055 - 114055
Published: March 22, 2024
Au-catalyzed
N,O-functionalization
of
1,4-diyn-3-ols
with
N-hydroxyanilines
provides
a
short
and
efficient
approach
to
construct
versatile
pyrrole
frameworks.
Using
DFT
calculations,
we
systematically
investigated
the
detailed
mechanisms
involved
in
this
reaction.
It
was
found
that,
commonly
asserted
NH/OH
activation
mechanism
unfavoured
due
high
energy
barrier.
The
main
reason
believed
be
associated
inversion
configuration
on
sp3-hybrid
C
atom
(generated
after
H(N)-shift)
which
results
significant
consumption
for
subsequent
H(O)-shift.
Therefore,
here
present
unique
"1,4-elimination/1,4-syn-protodeauration"
catalytic
mechanism,
(i)
charge
delocalization
carbon
cation
is
conductive
stability
1,4-elimination
TS;
(ii)
exergonicity
decreases
potential
surface
reaction;
(iii)
sp2-C
site
ensures
energy-efficient
retention
during
1,4-syn-protodeauration,
contrast
energy-consuming
classical
anti-protodeauration.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
88(1), P. 534 - 539
Published: Dec. 19, 2022
We
report
an
efficient
alkyl
transfer
strategy
for
the
direct
β-alkylation
of
chalcones
using
commercially
available
bromides
as
reagents.
In
this
transformation,
ortho-phosphanyl
substituent
in
is
crucial
controlling
their
reactivity
and
selectivity.
It
also
serves
a
reliable
shuttle
to
transform
electrophilic
into
nucleophilic
species
form
quaternary
phosphonium
salts
group
effectively
β-position
chalcones.
This
can
be
further
extended
alkenylation
benzaldehydes
assemble
functionalized
polyenes.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(21), P. 5428 - 5434
Published: Jan. 1, 2023
Herein,
the
first
example
of
umpolung
α-regioselective
1,3-dipolar
cycloaddition
optically
pure
perhydroindole-2-carboxylic
acid
1a
with
pyridinecarboxaldehydes
2
is
described.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
60(8), P. 992 - 995
Published: Dec. 21, 2023
Herein,
we
report
an
efficient
and
easily
operable
method
to
halohydroxylate
pyridiniums
through
interrupted
dearomative
reduction
strategy.
In
this
process,
make
the
most
of
halide
anion
from
pyridinium
salts
by
performing
reaction
in
DMSO
without
need
external
HX
added.
Notably,
changing
solvents
into
Et
New Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
48(37), P. 16151 - 16154
Published: Jan. 1, 2024
We
report
a
diastereoselective
dearomative
bifunctionalization
strategy
of
using
isoquinolinium
salts
to
access
bridged
tetrahydroisoquinolines
through
one-pot
three-component
cascade
process.
Journal of Physical Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
35(12)
Published: July 28, 2022
Abstract
The
[3
+
3]
cylcloaddition/annulation
is
an
important
complementary
for
construction
of
six‐membered
ring.
With
addition
organophosphine
to
the
Morita‐Baylis‐Hillman
(MBH)
carbonate,
a
potential
C3
synthon
can
be
furnished.
In
this
work,
catalytic
mechanisms
using
as
nucleophilic
or
electrophilic
dipole
react
with
cyclohexa‐2,5‐dienone‐substituted
benzenesulfonamide
are
studied
by
density
functional
theory
method.
computational
results
reveal
that
amide
anion
allylic
phosphonium
more
favorable
than
alkenyl
in
phosphorus
ylide.
Namely,
adduct,
rather
ylide
generated
deprotonation
phosphonium,
likely
act
dipole.
global
reactivity
index
calculations
indicate
species
involved
favored
pathway
have
better
reactivities
(both
nucleophilicity
and
electrophilicity),
especially
significantly
higher
anion.
