One-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter reaction to access 5-quaternary-4-amidocyclopent-2-enones and 2-quaternary-3-amidoindanones
Chemical Communications,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
one-pot
Nazarov
cyclization/oxidative
1,2-carbon
rearrangement/Ritter
reaction
has
been
explored
for
the
first
time,
facilitating
synthesis
of
unprecedented
2,3-disubstituted-5-quaternary-4-amidocyclopent-2-enone
and
2-quaternary-3-amidoindanones.
This
transformation
features
convenient
operation,
good
yields
(up
to
70%),
excellent
diastereoselectivity
20
:
1).
The
proposed
mechanism
is
supported
by
some
experimental
results.
Язык: Английский
From 5-HMF to Novel Cyclopentenone-Based Aza Spirocycles: An Intramolecular Aza-Piancatelli Reaction in Action
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(13), С. 9661 - 9665
Опубликована: Июнь 18, 2024
With
a
double
objective
to
upgrade
biobased
5-HMF
and
access
original
spirocycles
via
an
intramolecular
aza-Piancatelli
reaction,
multistep
sequence
was
designed
toward
appropriate
furylcarbinols.
The
impacts
of
both
the
nucleophiles,
arylamines
compared
alkoxyamines,
length
tether
were
studied.
After
in-depth
evaluation
different
parameters,
extension
scope
provided
library
azaspiro[4.5]non-8-en-7-ones
azaspiro[4.6]dec-3-en-2-ones
whose
skeletons
have
so
far
never
been
listed.
application
reaction
associated
with
use
HMF
in
fine
chemistry
gives
credit
development
novative
structures,
as
raised
by
green
community.
Combining
efforts
synthetic
methodology
integration
biosourced
platforms
could
open
way
new
molecules
exhibiting
properties
from
ones
petrochemical
sources.
Язык: Английский
Stereoselective Access to Spiro-isoindolinone Scaffolds via Catalytic Asymmetric aza-Piancatelli Rearrangement
Organic Letters,
Год журнала:
2024,
Номер
26(36), С. 7667 - 7671
Опубликована: Авг. 29, 2024
A
chiral
Brønsted
acid
catalyzed
asymmetric
aza-Piancatelli
rearrangement
of
3-furyl-3-hydroxyisoindolinones
with
anilines
has
been
developed,
enabling
the
divergent
construction
spiro-cyclopentenone-isoindolinones
in
high
yields
excellent
diastereo-
and
enantioselectivities
even
under
a
low
catalyst
loading
0.5
mol%.
Язык: Английский
Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH2 Group Alongside Unprotected Amines
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(45)
Опубликована: Июль 17, 2024
1,2-Diamination
of
alkenes
represents
an
attractive
way
to
generate
differentiated
vicinal
diamines,
which
are
prevalent
motifs
in
biologically
active
compounds
and
catalysts.
However,
existing
methods
usually
limited
scope
produce
diamines
where
one
or
both
nitrogens
protected,
adding
synthetic
steps
for
deprotection
further
N-functionalization
reach
a
desired
target.
Furthermore,
the
range
amino
groups
that
can
be
introduced
at
internal
position
is
fairly
limited.
Here
we
describe
1,2-diamination
styrenes
directly
installs
free
group
terminal
wide
variety
unprotected
nitrogen
nucleophiles
(primary
secondary
alkyl
aromatic
amines,
sulfoximines,
N-heterocycles,
ammonia
surrogate)
position.
Two
complementary
sets
conditions
encompass
electronically
activated
deactivated
with
diverse
substitution
patterns
functional
groups.
Moreover,
this
strategy
extended
1,2-aminothiolation
styrenes.
Язык: Английский
Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH2 Group Alongside Unprotected Amines
Angewandte Chemie,
Год журнала:
2024,
Номер
136(45)
Опубликована: Июль 17, 2024
Abstract
1,2‐Diamination
of
alkenes
represents
an
attractive
way
to
generate
differentiated
vicinal
diamines,
which
are
prevalent
motifs
in
biologically
active
compounds
and
catalysts.
However,
existing
methods
usually
limited
scope
produce
diamines
where
one
or
both
nitrogens
protected,
adding
synthetic
steps
for
deprotection
further
N‐functionalization
reach
a
desired
target.
Furthermore,
the
range
amino
groups
that
can
be
introduced
at
internal
position
is
fairly
limited.
Here
we
describe
1,2‐diamination
styrenes
directly
installs
free
group
terminal
wide
variety
unprotected
nitrogen
nucleophiles
(primary
secondary
alkyl
aromatic
amines,
sulfoximines,
N
‐heterocycles,
ammonia
surrogate)
position.
Two
complementary
sets
conditions
encompass
electronically
activated
deactivated
with
diverse
substitution
patterns
functional
groups.
Moreover,
this
strategy
extended
1,2‐aminothiolation
styrenes.
Язык: Английский
Calcium(II)‐Catalyzed Synthesis of Sulfoximinocyclopentenones
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 29, 2024
Abstract
A
series
of
4‐sulfoximinocyclopent‐2‐en‐1‐ones
was
prepared
in
35
to
99%
yield
through
a
calcium(II)‐catalyzed
aza‐Piancatelli
reaction,
including
enantioenriched
form.
Depending
on
their
substitution
pattern,
diverse
diastereoselective
chemical
transformations
can
be
applied
these
scaffolds,
allowing
access
cyclopentane
derivatives.
This
study
opens
synthetic
routes
cyclopentane‐based
scaffolds
and
also
paves
the
way
for
exploration
associated
space
drug
discovery.
Язык: Английский
Compartmentalizing Donor–Acceptor Stenhouse Adducts for Structure–Property Relationship Analysis
Cesar A. Reyes,
Alexander Karr,
Chloe A. Ramsperger
и другие.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 27, 2024
The
development
of
photoswitches
that
absorb
low
energy
light
is
notable
interest
due
to
the
growing
demand
for
smart
materials
and
therapeutics
necessitating
benign
stimuli.
Donor–acceptor
Stenhouse
adducts
(DASAs)
are
molecular
respond
in
visible
near-infrared
spectrum.
As
a
result
their
modular
assembly,
DASAs
can
be
modified
at
donor,
acceptor,
triene,
backbone
heteroatom
compartments
tuning
optical
photoswitching
properties.
This
Perspective
focuses
on
electronic
steric
contributions
each
compartment
how
they
influence
photophysical
properties
through
adjustment
isomerization
energetic
landscape.
An
emphasis
current
synthetic
strategies
limitations
highlights
opportunities
DASA
architecture,
thus
property
expansion.
Язык: Английский