Advances in the Synthesis of Cyclopropylamines
Chemical Reviews,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 6, 2025
Cyclopropylamines
are
an
important
subclass
of
substituted
cyclopropanes
that
combine
the
unique
electronic
and
steric
properties
with
presence
a
donor
nitrogen
atom.
In
addition
to
their
in
diverse
array
biologically
active
compounds,
cyclopropylamines
utilized
as
synthetic
intermediates,
particularly
ring-opening
or
cycloaddition
reactions.
Consequently,
synthesis
these
compounds
has
constituted
significant
research
topic,
evidenced
by
abundant
published
methods.
widely
used
Curtius
rearrangement,
classical
cyclopropanation
methods
have
been
adapted
integrate
function
(Simmons-Smith
reaction,
metal-catalyzed
reaction
diazo
on
olefins,
Michael-initiated
ring-closure
reactions)
advances
enantioselective
synthesis.
More
recently,
specific
developed
for
preparation
aminocyclopropane
moiety
(Kulinkovich
reactions
applied
amides
nitriles,
cyclopropenes,
involving
C-H
functionalization,
...).
The
topic
this
review
is
present
different
cyclopropylamine
derivatives,
aim
covering
methodological
best
possible,
highlighting
scope,
stereochemical
aspects
future
trends.
Язык: Английский
Spiro-Heterocycles: Recent Advances in Biological Applications and Synthetic Strategies
Tetrahedron,
Год журнала:
2025,
Номер
unknown, С. 134468 - 134468
Опубликована: Янв. 1, 2025
Язык: Английский
Highly stereo- and enantio-selective synthesis of spiro- cyclopropyl oxindoles via organic catalyst-mediated cyclopropanation
Chinese Chemical Letters,
Год журнала:
2025,
Номер
unknown, С. 110923 - 110923
Опубликована: Фев. 1, 2025
Язык: Английский
Synthesis of Highly Functionalized Indolizines via NIS-Promoted Spiroannulation/Ring-Opening Aromatization of Alkylidene Oxindoles with 2-(Pyridin-2-yl)acetate Derivatives
Luan-Ting Wu,
Honglin Diao,
Yi Wu
и другие.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 10, 2025
A
novel
NIS-promoted
domino
reaction
of
alkylidene
oxindoles
with
2-(pyridin-2-yl)acetate
derivatives
has
been
established,
enabling
the
efficient
and
straightforward
synthesis
a
vast
variety
highly
functionalized
indolizines
via
sequential
spiroannulation
ring-opening
aromatization
processes.
The
protocol
features
mild
conditions,
broad
substrate
scope,
high
efficiency,
scalability,
applicability
for
preparation
CF3-containing
indolizines.
Furthermore,
functional
groups
in
indolizine
framework
provide
feasibility
follow-up
derivatization.
Based
on
mechanistic
studies,
plausible
radical
mechanism
is
proposed
to
elucidate
formation
Язык: Английский
Nucleophile-Controlled Regiodivergent Domino Reactions of Enetriones with γ-Bromocrotonates: Access to 1,3-Dienic Esters and Tetrasubstituted Pyrans
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 23, 2025
Herein,
we
developed
an
efficient
nucleophile-controlled
regiodivergent
domino
reaction
between
enetriones
and
γ-bromocrotonates.
This
method
allowed
for
the
rapid
synthesis
of
a
range
1,3-dienic
esters
tetrasubstituted
pyrans
under
metal-free
conditions.
In
presence
pyridine,
SN2
substitution/Michael
addition/elimination
sequence
formed
in
satisfactory
yields
with
high
E-stereoselectivities.
Alternatively,
addition/cyclization/cyclopropanation/cyclopropane
ring-opening
process
forged
good
help
Et3N.
It
is
interesting
to
note
that
site-selective
reactions
γ-bromocrotonates
at
α-
or
γ-position
were
readily
realized
by
modulating
pyridine
Furthermore,
simple
Et3N
act
as
both
nucleophiles
substitution
Lewis
bases
deprotonation
processes.
Язык: Английский
Heteroatom-Controlled Three-Component [4 + 3] or [3 + 2] Annulation of Isatin-Derived Azomethine Ylide with Azadiene: Selective Synthesis of Spirooxindole-diazepines and Density Functional Theory Studies
Organic Letters,
Год журнала:
2024,
Номер
26(41), С. 8945 - 8950
Опубликована: Окт. 9, 2024
A
novel
three-component
[4
+
3]
annulation
reaction
of
isatin-derived
azomethine
ylides
with
azadienes
was
developed
for
the
first
time
to
efficiently
synthesize
spirooxindole-diazepines
incorporating
a
benzothiophene
moiety
under
catalyst-free
conditions.
Effects
heteroatom
azadiene
on
chemoselectivity
investigated.
With
use
bearing
benzofuran
as
substrate,
dominant
pathway
changed
an
α-[3
2]
annulation.
When
indenone
used,
distinct
γ-[3
observed.
Density
functional
theory
calculations
revealed
that
delicate
balance
between
kinetic
accessibility
and
thermodynamic
driving
force
controlled
competition
different
reactions.
Язык: Английский
Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates
Organic Letters,
Год журнала:
2024,
Номер
26(43), С. 9203 - 9209
Опубликована: Окт. 21, 2024
Controlling
the
selectivity
of
reactions
is
a
significantly
attractive
strategy
in
synthetic
organic
chemistry.
Herein,
an
efficient
base-controlled
chemodivergent
domino
reaction
between
o-aminochalcones
and
γ-bromocrotonates
has
been
developed.
A
series
cis-2,3-disubstituted
indolines
cyclopropane-fused
tetrahydroquinolines
were
obtained
via
two
pathways
with
broad
substrate
scope
moderate
to
excellent
yields
under
transition-metal-free
conditions.
It
noteworthy
that
could
be
used
as
C1
or
C2
synthons
by
modulating
base;
particular,
both
nucleophiles
electrophiles
generate
cyclopropanes
for
first
time.
Язык: Английский