The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(17), P. 11722 - 11734
Published: Aug. 15, 2022
In
this
study,
we
report
a
novel
and
efficient
synthetic
method
to
construct
isoquinolone
scaffold
via
the
Rh(III)-catalyzed
(4
+
2)
annulation
of
benzamide
with
an
unreported
coupling
reagent
methyl
2-chloroacrylate.
Accordingly,
other
valuable
1,2-benzothiazine
naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine
derivatives
are
also
obtained
through
similar
protocol.
Thus,
our
developed
is
highlighted
by
high
yield
reaction
versatility.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(12), P. 2356 - 2369
Published: Jan. 1, 2022
Enaminones
and
analogous
stable
enamines
are
well
known
as
platform
building
blocks
in
organic
synthesis
for
the
construction
of
heterocyclic
compounds,
especially
N-heterocycles.
To
date,
enaminones
have
been
successfully
employed
various
5-
or
6-
membered
heterocycles.
Recently,
synthetic
protocols
accomplished
by
diversity-oriented
annulation
reactions
based
on
C-N
bond
cleavage
gained
notable
success.
In
this
review,
development
transition
metal-free
product
featuring
a
is
reviewed.
Green Chemistry,
Journal Year:
2022,
Volume and Issue:
24(13), P. 5058 - 5063
Published: Jan. 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.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(12), P. 2404 - 2408
Published: March 18, 2022
A
practical
method
for
the
synthesis
of
2,2-difluorinated
2,3-dihydrofurans
has
been
established
via
[4
+
1]
annulation
enaminones
and
BrCF2CO2Et
with
Na2CO3
promotion.
This
new
protocol
does
not
employ
any
transition
metal
reagent
enables
annulative
difluoromethylation
by
partial
cleavage
C═C
double
bond.
In
addition,
further
treatment
hydrochloric
acid
in
one
pot
leads
to
β-keto
enoic
acids
(4-oxo-2-butenoic
acids)
a
formal
enaminone
C-N
carboxylation.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(47), P. 8451 - 8456
Published: Nov. 16, 2023
The
three-component
reactions
of
enaminones,
disulfides,
and
alcohols
for
the
synthesis
polyfunctionalized
alkenes
have
been
realized
via
C-H
C-N
bond
transformation
on
enaminones.
proceed
in
a
novel
"alkene-to-alkene"
difunctionalization
mode
without
using
any
transition
metal.
application
alkene
products
divergent
sulfenyl
heteroaryls,
including
sulfenylated
pyrazoles,
pyrimidines,
isoxazoles,
simple
annulation
has
also
verified.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(7), P. 4833 - 4838
Published: March 22, 2023
A
facile
and
practical
method
for
the
synthesis
of
fused
tricyclic
pyrazolo[5,1-a]isoquinolines
has
been
realized
via
reactions
enaminones,
hydrazine
hydrochloride,
internal
alkynes.
By
means
Rh
catalysis,
extraordinary
high-order
bond
functionalization,
including
transformation
aryl
C–H,
ketone
C═O,
alkenyl
C–N
bonds
in
marks
major
feature
cascade
reactions.
The
results
disclose
individual
advantage
enaminones
design
novel
efficient
synthetic
methods.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(19), P. 13195 - 13203
Published: Sept. 15, 2022
Visible
light
photocatalytic
reactions
of
NH2-enaminones
and
ammonium
thiocyanate
for
chemoselective
α-C-H
thiocyanation
have
been
realized
the
first
time,
providing
a
sustainable
route
synthesis
thiocyanated
NH2-enaminones.
In
addition,
enaminone
products
can
be
flexibly
transformed
into
2-aminothiazoles
2-thiazolinones
via
simple
operation.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(45), P. 6885 - 6888
Published: Jan. 1, 2023
The
annulation
reactions
of
enaminones
with
quinonediimides/quinoneimides
for
the
selective
synthesis
indoles
and
2-aminobenzofurans
have
been
realized.
With
Zn(II)
catalysis,
quinonediimides
reacted
to
give
via
HNMe2-elimination-based
aromatization.
Fe(III)
quinoneimides
provided
a
key
dehydrogenative
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.
