The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(17), С. 11722 - 11734
Опубликована: Авг. 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.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(15), С. 2601 - 2606
Опубликована: Июль 12, 2023
Abstract
A
copper‐catalyzed
olefinic
C(
sp
2
)−H
activation/carbene
insertion/ester
hydrolysis/cyclization
sequence
has
been
developed
for
the
synthesis
of
substituted
2(5
H
)‐furanones
employing
readily
available
enaminones
and
aryl
diazo
esters
as
substrates.
This
method
features
operationally
simple
good
functional
group
tolerance.
The
transformation
could
be
scaled
up
to
gram
quantities
obtained
)‐furanone
derivatives
easily
converted
a
wide
range
useful
synthetic
building
blocks,
indicative
applicability
strategy.
Isotope
labeling
experiments
demonstrated
ester
was
hydrolyzed
during
reaction.
Abstract
Nitrogen‐containing
heterocycles
represent
fundamental
components
found
in
a
myriad
of
natural
compounds,
pharmaceuticals,
tailored
bioactive
substances,
and
agrochemicals.
In
recent
decades,
the
field
synthetic
chemistry
has
prioritized
these
directing
considerable
research
endeavour
toward
developing
efficient
concise
methodologies
for
their
synthesis.
Consequently,
there
is
growing
interest
pioneering
novel
approaches
to
fabricate
immensely
coveted
structural
motifs.
Transition
metal‐catalyzed
reactions
leveraging
solvents
as
carbon
(C1)
synthons
offer
notable
advantages,
including
streamlined
processes,
enhanced
atom
economy,
environmental
sustainability.
This
review
sheds
light
on
advancements
utilization
collective
such
methanol
(alongside
other
alcohols),
N,N
‐dimethylethanolamine
(DMEA),
triethylamine
(TEA)
(in
conjunction
with
amines),
tetrahydrofuran
(THF),
toluene,
dichloromethane
(DCM),
dimethyl
sulfoxide
(DMSO),
dimethylformamide
(DMF)
C1
synthons,
serving
foundational
units
synthesis
N
‐heterocycles,
quinazolinone,
quinazoline,
quinoxaline,
pyridine,
pyrimidine,
among
others.
Various
reaction
conditions
employing
diverse
transition
metals,
coupling
partners,
or
reagents,
reported
literature,
have
been
explored.
Applied Organometallic Chemistry,
Год журнала:
2024,
Номер
38(9)
Опубликована: Июль 5, 2024
A
novel
Rh‐catalyzed
three‐component
synthesis
of
N
‐(
o
‐alkylaryl)
pyrazoles
via
cascade
pyrazole
annulation
and
aryl
C‐H
conjugate
addition
to
alkenes
has
been
developed
with
enaminones,
hydrazines,
functionalized
as
starting
materials.
The
raw
materials
used
in
this
reaction
are
simple,
cheap,
readily
available,
the
reactions
feature
excellent
step
economy
by
furnishing
products
formation
a
ring
key
activation
one‐step
operation.
Moreover,
proceeds
smoothly
under
air
atmosphere,
making
it
easy
operate.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(19), С. 5532 - 5537
Опубликована: Янв. 1, 2024
Chemodivergent
synthesis
of
polysubstituted
pyrroles
and
pyridines
from
N
-allyl
enaminones
via
tandem
site-selective
bromination
the
highly
regioselective
Heck
reaction.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(17), С. 11722 - 11734
Опубликована: Авг. 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.
