Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(29), С. 19660 - 19666
Опубликована: Июль 12, 2024
Late-stage
derivatization
of
drug-like
functional
groups
can
accelerate
drug
discovery
efforts
by
swiftly
exchanging
hydrogen-bond
donors
with
acceptors,
or
modulating
key
physicochemical
properties
like
logP,
solubility,
polar
surface
area.
A
proven
strategy
to
improve
ligand
potency
is
extend
the
displace
water
molecules
that
are
mediating
interactions
a
receptor.
Inspired
this
application,
we
developed
method
regioselectively
transmute
nitrogen
atom
from
pyridine
into
carbon
bearing
an
ester,
flexible
group
handle.
We
applied
variety
substituted
pyridines,
as
well
late-stage
transformation
FDA-approved
drugs.
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Май 4, 2024
Abstract
Developing
skeletal
editing
tools
is
not
a
trivial
task,
and
realizing
the
corresponding
single-atom
transmutation
in
ring
system
without
altering
size
even
more
challenging.
Here,
we
introduce
strategy
that
enables
polycyclic
arenols,
highly
prevalent
motif
bioactive
molecules,
to
be
readily
converted
into
N
-heteroarenes
through
carbon–nitrogen
transmutation.
The
reaction
features
selective
nitrogen
insertion
C–C
bond
of
arenol
frameworks
by
azidative
dearomatization
aryl
migration,
followed
ring-opening,
ring-closing
(ANRORC)
achieve
carbon-to-nitrogen
aromatic
framework
arenol.
Using
widely
available
arenols
as
-heteroarene
precursors,
this
alternative
approach
allows
streamlined
assembly
complex
heteroaromatics
with
broad
functional
group
tolerance.
Finally,
pertinent
transformations
products,
including
synthesis
biheteroarene
skeletons,
were
conducted
exhibited
significant
potential
materials
chemistry.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(21), С. 2656 - 2667
Опубликована: Июль 16, 2024
Comprehensive
Summary
Nitrenes,
as
neutral
monovalent
nitrogen‐centered
molecular
species,
can
insert
into
various
bond
or
remove
nitrogen
atoms
from
amines.
Nitrene
assisted
single‐atom
skeletal
editing,
discovered
decades
ago,
provides
an
efficient
approach
for
the
precise
alteration
of
cyclic
skeletons.
In
this
review,
we
briefly
summarize
early
studies
on
editing
frameworks
involving
nitrene
and
introduce
several
recent
important
advances
systematically.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(25), С. 16963 - 16970
Опубликована: Май 1, 2024
Despite
the
significant
achievements
in
dearomatization
and
C–H
functionalization
of
arenes,
arene
ring-opening
remains
a
largely
unmet
challenge
is
underdeveloped
due
to
high
bond
dissociation
energy
strong
resonance
stabilization
inherent
aromatic
compounds.
Herein,
we
demonstrate
novel
carbene
assisted
strategy
for
ring-opening.
The
understanding
mechanism
by
our
DFT
calculations
will
stimulate
wide
application
bulk
chemicals
synthesis
value-added
polyconjugated
chain
molecules.
Various
aryl
azide
derivatives
now
can
be
directly
converted
into
valuable
enynes,
avoiding
traditional
including
multistep
unsaturated
precursors,
poor
selectivity
control,
subsequent
transition-metal
catalyzed
cross-coupling
reactions.
simple
conditions
required
were
demonstrated
late-stage
modification
complex
molecules
fused
ring
This
chemistry
expands
horizons
provides
pathway
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(29), С. 19660 - 19666
Опубликована: Июль 12, 2024
Late-stage
derivatization
of
drug-like
functional
groups
can
accelerate
drug
discovery
efforts
by
swiftly
exchanging
hydrogen-bond
donors
with
acceptors,
or
modulating
key
physicochemical
properties
like
logP,
solubility,
polar
surface
area.
A
proven
strategy
to
improve
ligand
potency
is
extend
the
displace
water
molecules
that
are
mediating
interactions
a
receptor.
Inspired
this
application,
we
developed
method
regioselectively
transmute
nitrogen
atom
from
pyridine
into
carbon
bearing
an
ester,
flexible
group
handle.
We
applied
variety
substituted
pyridines,
as
well
late-stage
transformation
FDA-approved
drugs.
