European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(32)
Published: July 6, 2023
Abstract
The
divergent
synthesis
of
dihydropyrimidouracil
and
pyrimidouracil
derivatives
from
N
‐uracil
amidines
tertiaryamines
by
an
oxidative
C(sp
3
)−
cleavage
cascade
cyclization
reaction
is
first
described.
This
transformation
enables
the
formation
new
2
bonds
via
selection
different
oxidation
conditions.
features
this
method
include
tunable
product
selectivity,
excellent
chemoselectivity,
readily
available
starting
materials,
broad
substrate
scope,
good
tolerance
functional
groups,
moderate
to
high
yields.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(40), P. 7298 - 7303
Published: Oct. 3, 2023
An
unprecedented
protocol
for
a
Rh(III)-catalyzed
[3
+
2]
annulation
from
simple
and
readily
available
enaminones
iodonium
ylides
has
been
developed.
The
novel
strategy
allows
access
to
new
class
of
structurally
diverse
tetrahydro-indolones
with
high
efficiency
broad
substrate
scope.
In
addition,
this
transformation
represents
the
first
example
selective
alkenyl
C–H
bond
functionalization
enaminones.
Finally,
potential
applications
are
demonstrated
through
gram-scale
reaction
late-stage
modification.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(39), P. 7214 - 7219
Published: Sept. 26, 2023
A
novel
Rh(III)-catalyzed
cascade
alkenyl
C-H
activation/[3
+
2]
annulation/pinacol
rearrangement
reaction
of
enaminones
with
iodonium
ylides
has
been
developed.
This
methodology
provides
a
new
and
straightforward
synthetic
strategy
to
afford
highly
functionalized
2-spirocyclo-pyrrol-3-ones
in
satisfactory
yield
from
readily
available
starting
materials
under
mild
conditions.
Moreover,
gram-scale
reactions
further
derivatization
experiments
are
implemented
demonstrate
the
potential
utility
this
developed
approach.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(22), P. 5660 - 5666
Published: Jan. 1, 2023
Highly
functionalized
3a,7a-dihydroxy
hexahydro-4
H
-indol-4-ones
were
efficiently
synthesized
via
a
Ru(
iii
)-catalyzed
alkenyl
C(sp
2
)–H
bond
functionalization/[3
+
2]
annulation
reaction
between
readily
available
enaminones
and
iodonium
ylides.
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(15), P. 1727 - 1733
Published: March 26, 2024
Comprehensive
Summary
Chemodivergent
synthesis
of
benzofurans
and
2,3‐dihydrobenzofurans
has
been
realized.
Under
a
reaction
system
consisting
DBDMH
K
2
CO
3
as
promotors,
controlled
conditions
enabled
the
formation
two
sets
valuable
heterocycles
from
tandem
transformation
enaminones
salicylaldehydes.
The
key
to
success
was
identification
parameters,
in
which
imine
intermediate
formed
by
transient
halogenation
coupling
substitution
processes
underwent
either
aldol
condensation/annulation
or
hydrolysis/aldol
condensation.
additives
NH
4
Cl
Fe
(SO
)
unique
selectivity
this
reaction.
A
broad
substrate
scope
salicylaldehydes
employed
reaction,
demonstrating
excellent
functional
group
tolerance
versatility.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(15), P. 11060 - 11066
Published: July 24, 2024
Reported
herein
is
a
new
photocatalytic
annulation
for
the
synthesis
of
2,3,4,6-tetrasubstituted
pyridines
with
enaminones
and
N,N,N′,N′-tetramethyl
ethylenediamine
(TMEDA).
The
reactions
take
place
without
requiring
transition
metal
reagent
provide
products
broad
scope.
methyl
in
TMEDA
acts
as
carbon
source
pyridine
ring
construction,
BrCF2CO2Et
plays
role
terminal
oxidant
free
radical
quenching.
Synthesis,
Journal Year:
2024,
Volume and Issue:
56(16), P. 2565 - 2571
Published: April 26, 2024
Abstract
Visible-light
photocatalytic
reactions
between
enaminones
and
thioureas
leading
to
thiazole
products
have
been
achieved.
The
annulation
process
consists
of
tandem
C–S
C–N
bond
formation
by
running
under
air
atmosphere
at
ambient
temperature.
Broad
substrate
tolerance
the
sustainable
protocol
has
verified
practical
synthesis
divergent
thiazoles
with
both
monocyclic
fused
cyclic
structures.
β-Enaminone
transformation
strategies
are
widely
employed
in
the
synthesis
of
numerous
biologically
active
drugs
and
natural
products,
highlighting
their
significance
medicinal
chemistry.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(16), P. 11627 - 11636
Published: Aug. 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.
