New Journal of Chemistry,
Год журнала:
2024,
Номер
48(26), С. 11682 - 11687
Опубликована: Янв. 1, 2024
A
novel
synthesis
method
has
been
developed
for
the
construction
of
2,4-diarylpyridines.
The
reaction
includes
reduction,
Michael
addition,
decarboxylation,
intramolecular
cyclization,
oxidation,
ring-opening
and
aromatization
reaction.
Green Chemistry,
Год журнала:
2022,
Номер
24(13), С. 5058 - 5063
Опубликована: Янв. 1, 2022
The
electrochemical
annulation
of
enaminones/analogous
enamines
and
thioureas
providing
2-aminothiazoles
has
been
realized.
Modulating
the
electrolyte
enables
diastereoselective
synthesis
4,5-dialkoxyl
thiazolines
by
dearomatization.
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(28)
Опубликована: Фев. 24, 2023
Using
benzylamines
as
the
C4
source
of
1,4-dihydropyridines
(1,4-DHPs),
a
Cu-catalyzed
oxidative
[1+2+1+2]
cascade
cyclization
for
synthesis
1,4-DHPs
was
firstly
developed.
A
broad
range
easily
available
N,N-dimethyl
enaminones
and
are
employed
smoothly
to
provide
diverse
with
high
efficiency.
This
method
is
performed
by
one-pot
C(sp3
)-H
bond
functionalization/C(sp3
)-N
cleavage/cyclization
strategy
form
simultaneously
two
)-C(sp2
)
bonds,
C(sp2
1,4-DHP
ring.
Scientific Reports,
Год журнала:
2022,
Номер
12(1)
Опубликована: Сен. 8, 2022
Abstract
The
objective
of
this
study
was
to
design
new
polysubstituted
pyrrole
derivatives
as
selective
acetylcholinesterase
(AChE)
inhibitors
target
Alzheimer's
disease.
In
context,
a
highly
efficient,
one-pot,
sequential,
multi-component
synthesis
diverse
range
pyrroles
developed
through
sequential
domino
strategy
by
the
condensation
amines
with
1,1-bis(methylthio)-2-nitroethene
(BMTNE),
Knovenagle
reaction
arylglyoxals
malono
and
subsequent
Michael
addition
intramolecular
cyclization
in
EtOH
at
reflux
.
Thirty-nine
synthesized
compounds
were
evaluated
AChE
butyrylcholinesterase
(BChE)
inhibitors.
Among
compounds,
compound
4ad
(IC
50
=
2.95
±
1.31
µM)
most
potent
inhibitor
no
significant
inhibition
against
BChE.
A
kinetic
revealed
that
inhibited
an
uncompetitive
mode.
Based
on
molecular
modeling
study,
due
its
small
size
properly
fitted
into
active
site
compared
BChE
stabilized
H-bond
hydrophobic
interactions
critical
residues
binding
pocket.
Consequently,
it
proposed
derivative
can
be
ideal
lead
candidate
AD
simple
practical
operation
synthetic
procedures.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(24), С. 4440 - 4446
Опубликована: Дек. 2, 2022
Abstract
A
silver‐catalyzed
protocol
for
the
synthesis
of
3‐(1
H
‐isochromen)‐chromones
is
described.
The
method
involves
an
initial
6‐endo‐dig
cyclization
o
‐alkynylbenzaldehydes
and
domino
C−H
alkylation
chromone
annulation
‐hydroxyarylenaminones,
which
enables
installation
1
‐isochromen
in
a
single
structure.
This
synthetic
strategy
advantageous
excellent
regioselectivity,
step
economy,
concise
one‐pot
methodology,
gram‐scale
synthesis,
as
well
high
bond‐forming
efficiency.
magnified
image
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(8), С. 1217 - 1223
Опубликована: Март 25, 2023
Abstract
An
oxidative
[3+2+1]
cyclization
of
enaminones
and
N
‐alkenyl‐2‐pyrrolidinone
is
described
for
the
synthesis
4‐alkylated
1,4‐dihydropyridines
(1,4‐DHPs).
By
using
terminal
olefin
as
C4
source
1,4‐DHP
skeleton,
this
synthetic
strategy
provides
a
series
1,4‐DHPs
through
1,1‐difunctionalization/cyclization
process.
In
protocol,
two
C(
sp
3
)−C(
2
)
bonds
)−N
bond
are
simultaneously
formed,
hydrogen
on
newly
formed
methyl
group
skeleton
confirmed
possible
mechanism
proposed.
magnified
image
Chemical Communications,
Год журнала:
2023,
Номер
59(9), С. 1217 - 1220
Опубликована: Янв. 1, 2023
A
novel
protocol
for
the
synthesis
of
highly
functionalized
benzo[b][1,5]diazocin-6(5H)-one
derivatives
(BDCOs,
4
and
5)
from
2-aryl-1H-indoles
1,1-enediamines
was
developed
via
a
complex
cascade
reactions
including
regioselective
free
radical
oxidation,
1,2-addition
imine,
imine-enamine
tautomerization,
intramolecular
cyclization,
ring
expansion.
The
reaction
enabled
by
refluxing
mixture
two
substrates
in
presence
di-tert-butyl
peroxide
(DTBP)
as
an
oxidant
anhydrous
CuI
catalyst
toluene
under
argon
protection.
Consequently,
series
BDCOs
(4
were
synthesized
with
high
regioselectivity
good
yield.
This
can
be
used
one-pot
oxidative
annulation
rather
than
multi-step
reaction,
which
is
suitable
both
combinatorial
parallel
syntheses
BDCOs.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2190 - 2199
Опубликована: Янв. 27, 2024
Ketenimines
represent
an
important
class
of
reactive
species,
useful
synthetic
intermediates,
and
synthons.
However,
in
general,
ketenimines
preferentially
undergoes
nucleophilic
addition
reactions
with
hydroxyl
amino
groups,
carbon
functional
groups
remain
a
less
studied
subset
such
systems.
Herein,
we
develop
straightforward
syntheses
pyridin-4(1H)-imines
that
is
achieved
by
cyclization
reacting
enaminone
unit
α-acylketenimine
which
generated
from
the
sulfonyl
azides
terminal
ynones
situ
(CuAAC/Ring
cleavage
reaction).
The
cascade
process
starts
α-C
instead
group,
attacking
electron-deficient
central
ketenimine,
chemoselectivity
unconventional
products
were
formed
intramolecular
cyclization.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(15), С. 4078 - 4084
Опубликована: Янв. 1, 2022
Highly
functionalized
5-alkylidene-3-pyrrolin-2-ones
were
efficiently
synthesized
via
a
four-component
cascade
cyclization/sulfonylation
reaction
between
readily
available
2,4-pentanediones,
primary
amines
and
sodium
sulfinates
under
mild
conditions.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(16), С. 11627 - 11636
Опубликована: Авг. 9, 2023
Syntheses
of
highly
functionalized
4-alkylated
1,4-dihydropyridines
(1,4-DHPs)
from
cyclic
ethers
and
enaminones
via
iron(II)-mediated
oxidative
free
radical
cascade
C(sp3)-H
bond
functionalization/C(sp3)-O
cleavage/cyclization
reaction
have
been
first
developed.
This
novel
synthetic
strategy
offers
an
alternative
method
for
the
construction
1,4-DHPs
by
using
esters
as
C4
sources,
well
expands
application
in
heterocycle
synthesis.