Cascade Oxypalladation/1,3-Palladium Shift to Access Cyclopentene-Fused Isocoumarins
Organic Letters,
Год журнала:
2024,
Номер
26(30), С. 6353 - 6358
Опубликована: Июль 23, 2024
Fused
isocoumarins
are
frequently
found
in
several
natural
products
and
pharmaceuticals.
Herein,
a
cascade
annulation
of
2-alkynylbenzoate-tethered
cyclic
1,3-diones
via
sequential
Язык: Английский
Polyfluorinated benzoic acids as promising reagents for organic synthesis and medicinal chemistry
Russian Chemical Reviews,
Год журнала:
2024,
Номер
93(8), С. RCR5131 - RCR5131
Опубликована: Авг. 1, 2024
Polyfluoroaromatic
compounds
occupy
a
special
place
in
organic
synthesis
due
to
wide
range
of
their
chemical
transformations
and
unique
biological
properties.
The
introduction
the
carboxyl
function
into
polyfluoroarenes
allows
further
diversification
chemistry
these
compounds.
This
review
summarizes
data
on
polyfluorobenzoic
acids,
including
derivatives
polyfluorosalicylic
acids.
reactions
esterification,
amidation,
reduction,
decarboxylation,
metal-catalyzed
decarboxylative
cross-coupling,
C–H
functionalization,
reductive
defluorination,
nucleophilic
aromatic
substitution,
heterocyclization
complex
formation
are
considered.
Reactivity
features
polyfluorobenzoates
comparison
non-fluorinated
counterparts
highlighted.
potential
for
practical
applications
acid
derivatives,
primarily
as
biologically
active
compounds,
is
presented.
<br>
Bibliography
includes
300
references.
Язык: Английский
Asymmetric Total Synthesis of Naturally Occurring (R)-2′-Methoxydihydroartemidin, (R)-(E)-3′-Hydroxyartemidin, and Its Structural Congeners: Method Optimization and Mechanistic Analysis
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(21), С. 15764 - 15776
Опубликована: Окт. 18, 2024
Asymmetric
total
synthesis
of
naturally
occurring
3-substituted
isocoumarins,
2′-methoxydihydroartemidin,
(E)-3′-hydroxyartemidin,
and
two
structural
congeners
is
reported
in
this
article.
Enantiopure
3-alkylisocoumarin
core
present
those
target
molecules
was
accessed
through
an
atom-economical
regiodefined
6-endo-dig
cyclization
from
properly
substituted
2-halobenzoic
acids
chiral
terminal
alkynes
ligand-free
Cu(I)
catalysis.
A
detailed
mechanistic
investigation
carried
out
control
experiments,
density
functional
theory
(DFT)
analysis
reveals
that
solvent
directed
a
non-Sonogashira
pathway
direct
insertion
alkyne
way
operating.
The
synthesized
3-alkylisocoumarins
are
synthetically
manipulated
into
various
small
molecular
entities.
Язык: Английский
Ru(II)-Catalyzed Decarboxylative (4 + 2)-Annulation of Benzoic Acids and Benzamides with Propargyl Cyclic Carbonates
Organic Letters,
Год журнала:
2024,
Номер
26(36), С. 7590 - 7595
Опубликована: Сен. 3, 2024
Propargyl
cyclic
carbonates
have
emerged
as
versatile
precursors
in
synthetic
chemistry.
However,
their
reactivity
has
so
far
been
limited
to
transition
metal-catalyzed
substitution
and
cyclization
reactions.
Herein,
we
illustrate
the
successful
employment
of
propargyl
coupling
partners
Ru(II)-catalyzed
C-H
annulation
benzoic
acids
benzamides.
This
approach
allowed
us
access
a
broad
range
biologically
relevant
isocoumarin
isoquinolinone
derivatives
good
excellent
yields,
utilizing
bench-stable
easily
accessible
precursors.
Preliminary
mechanistic
studies
indicated
that
metalation
step
is
both
reversible
rate-determining
reaction
pathway.
Furthermore,
utility
developed
methodology
illustrated
by
scale-up
postfunctionalization
experiments.
Язык: Английский
Non-Kolbe Oxidation Driven Electrochemical C(sp2)-H Lactonization towards the Synthesis of Isocoumarins
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(23), С. 6742 - 6747
Опубликована: Янв. 1, 2024
A
novel
method
for
electrochemical
C(sp
2
)–H
lactonization
was
developed.
Язык: Английский
Synthesis of 4-Fluoroisocoumarins by Copper-Catalyzed Annulation of 2-Halobenzoic Acids and 2-Fluoro-1,3-diketones
Journal of Fluorine Chemistry,
Год журнала:
2024,
Номер
280, С. 110355 - 110355
Опубликована: Окт. 9, 2024
Язык: Английский
Synthesis of diarylsulphide/diarylselenide embedded pyrazole-fused isocoumarins and isatin/ninhydrin hydrazones via acid catalyzed solvent and temperature controlled reactions
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 11, 2024
Room
temperature
stirring
of
a
mixture
chalcogenated
arylhydrazones
and
ninhydrin
in
dichloromethane
(DCM)
the
presence
acid
leads
to
formation
pyrazole-fused
isocoumarins,
substituted
with
diarylsulphide/diarylselenide
moiety.
On
other
hand,
refluxing
same
protic
polar
solvent
ethanol
produces
containing
hydrazones.
Further
study
reveals
that,
like
ninhydrin,
isatin
can
also
generate
corresponding
hydrazones
at
C-3
position
under
similar
reaction
conditions.
Язык: Английский
Novel Metal-Free Synthesis of 3-Substituted Isocoumarins and Evaluation of Their Fluorescence Properties for Potential Applications
Molecules,
Год журнала:
2024,
Номер
29(11), С. 2449 - 2449
Опубликована: Май 23, 2024
A
novel
metal-free
synthesis
of
3-substituted
isocoumarins
through
a
sequential
O-acylation/Wittig
reaction
has
been
established.
The
readily
accessible
(2-carboxybenzyl)-triphenylphosphonium
bromide
and
diverse
chlorides
produced
various
1H-isochromen-1-one
in
the
presence
triethylamine,
employing
O-acylation
an
intramolecular
Wittig
acid
anhydride.
Reactions
using
these
facile
conditions
have
exhibited
high
functional
group
tolerance
excellent
yields
(up
to
90%).
Moreover,
fluorescence
properties
isocoumarin
derivatives
were
evaluated
at
theoretical
experimental
levels
determine
their
potential
application
fluorescent
materials.
These
good
photoluminescence
THF
with
large
Stokes
shift
absolute
quantum
yield
up
14%.
Язык: Английский