Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(15), P. 2536 - 2544
Published: Feb. 24, 2023
Abstract
In
this
study,
regio‐
and
diastereoselective
ring‐opening
cyclization
of
spirocyclopropanes
with
phosphorus
ylides
stabilized
by
electron‐withdrawing
groups
were
developed.
The
reaction
various
cyclohexane‐1,3‐dione‐2‐spirocyclopropanes
bearing
alkoxycarbonyl
proceeded
smoothly
without
any
additives
to
provide
the
corresponding
6,7‐dihydroindan‐4‐ones
in
32–87%
yields.
Cycloheptane‐1,3‐dione‐2‐spirocyclopropanes
also
used
reaction,
producing
products
1,2,3,6,7,8‐hexahydroazulen‐4‐ones
52–67%
resulting
[5.6]‐
[5.7]‐fused
carbocyclic
readily
converted
into
highly
substituted
indanes
azulenes,
respectively,
oxidation.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(26), P. 5482 - 5487
Published: June 24, 2024
An
efficient
synthesis
of
quinoxaline-fused
aza-bicyclo[2.1.1]hexanes
bearing
multiple
quaternary
carbon
centers
via
the
intermolecular
[2π+2σ]
cycloaddition
bicyclo[1.1.0]butanes
and
quinoxalin-2(1H)-ones,
facilitated
by
Lewis
acid
catalysis,
is
presented.
This
reaction
carried
out
under
mild
conditions
exhibits
a
broad
substrate
scope
excellent
functional
group
tolerance.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(39), P. 7118 - 7122
Published: Sept. 25, 2022
Herein,
a
photoinitiated
radical
relay
reaction
of
quinoxalin-2(1H)-ones,
with
acyloxy
nitroso
compounds
as
source
radicals,
is
described.
Although
the
C-H
functionalization
quinoxalin-2(1H)-ones
has
been
investigated,
its
difunctionalization,
simultaneous
construction
C-C
and
N-N
bonds
directly
via
reaction,
rarely
reported.
Moreover,
obtained
products
underwent
sequential
reactions
to
access
C7-NO2
under
mild
conditions.
Synthesis,
Journal Year:
2023,
Volume and Issue:
55(23), P. 3875 - 3894
Published: May 22, 2023
Abstract
This
review
discusses
the
utility
of
donor-acceptor
cyclopropanes
(DACs)
for
construction
heterocycles.
In
addition
to
(3+2),
(3+3),
and
(4+3)
cycloaddition
pathways,
nucleophilic
ring-opening
reactions,
intramolecular
transformations,
cycloisomerizations
in
presence
suitable
catalysts
pave
way
generation
heterocycles
from
DACs.
The
mild
reactions
conditions
employed
variety
starting
materials
that
can
be
used
as
reaction
partners
make
DAC
route
heterocycle
synthesis
attractive.
literature
covered
this
is
period
2018
2023.
1
Introduction
2
Synthesis
Nitrogen
Heterocycles
2.1
By
Annulations
with
Anthranils
Azadienes
2.2
Nucleophilic
Attack
Anilines
Hydrazones
2.3
Reaction
Ureas
Thioureas
2.4
Annulation
Reactions
Using
an
Azomethine
Imine
2.5
Other
2.6
Transformations
3
Oxygen
3.1
Intramolecular
3.2
Intermolecular
4
Sulfur
Selenium
4.1
Thiocarbonyl
Substrates
4.2
Thio-
Selenocyanates
Thiosulfonate
Salts
5
N–S
N–O
6
Conclusions
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(16), P. 10890 - 10901
Published: Aug. 2, 2022
MgI2-catalyzed
nucleophilic
ring-opening
reactions
of
donor-acceptor
cyclopropanes
with
indoline-2-thiones
as
easy-to-handle
sulfur
nucleophiles
were
investigated.
A
series
functionalized
γ-indolylthio
butyric
acid
derivatives
synthesized
in
good
to
excellent
yields
under
mild
reaction
conditions.
Furthermore,
the
thioether
products
could
be
transformed
sulfone
and
methionine
analogues.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(2), P. 1147 - 1154
Published: Jan. 11, 2023
A
new
methodology
for
the
synthesis
of
tetrahydroimidazo[1,5-a]quinoxalin-4(5H)-ones
has
been
accomplished
through
annulation
quinoxalin-2(1H)-ones
initiated
by
electrochemical
decarboxylation
N-arylglycines
catalyzed
ferrocene.
With
a
pair
oxidative
and
reductive
processes
occurring
among
substrates
intermediates
instead
on
electrodes,
electricity
consumption
was
decreased.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(8), P. 1948 - 1958
Published: Jan. 1, 2023
The
mechanism
and
stereoselectivity
of
the
Ni-catalyzed
[3
+
3]
annulation
between
donor–acceptor
cyclopropanes
(DACs)
diaziridines
were
rationalized
by
DFT
calculations.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 24, 2025
The
asymmetric
catalytic
[3+2]
cycloannulation
of
benzoxazinones
with
isatin-derived
ketimines
for
the
efficient
construction
imidazo[5,1-c]oxazinones
has
been
developed,
which
realized
first
reaction
excellent
stereoselectivities.
A
series
containing
three
stereogenic
centers
one
gem-diamine-type
spiro
tetrasubstituted
center
were
obtained
in
this
organocatalytic
good
yields
and
high
functional
group
tolerance.
Journal of Heterocyclic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 23, 2025
ABSTRACT
A
simple
method
has
been
developed
to
prepare
tetrahydro‐5H‐chromeno[4,3‐
c
]pyridazin‐5‐ones
by
reacting
donor‐acceptor
cyclopropane
1,1‐dieters
with
salicylaldehyde
phenylhydrazones
in
the
presence
of
Cu(OTf)
2
,
yielding
moderate
results
excellent
diastereoselectivity.
Moreover,
control
experiments
revealed
that
reaction
proceeds
via
a
tandem
[3
+
3]‐annulation/lactonization
mechanism.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(14), P. 2403 - 2415
Published: June 16, 2022
Abstract
We
report
a
procedure
for
the
multigram
synthesis
of
4‐(dimethylamino)pyridinium
azide,
stable,
non‐explosive,
low‐hygroscopic
source
azide
ion
soluble
in
both
protic
and
aprotic
organic
solvents.
In
ionic
liquid
media
this
reagent
was
shown
to
serve
as
safer
equivalent
toxic
unstable
hydrazoic
acid.
The
synthetic
utility
system
demonstrated
using
donor‐acceptor
cyclopropane
ring
opening
model
process.
General
procedures
furnishing
variety
dialkyl
(2‐azido‐2‐arylethyl)malonates
or
4‐azido‐4‐arylbutyrates,
depending
on
applied,
were
elaborated.
conversion
times
studied
cyclopropanes
established
providing
relative
reactivity
sequence.
application
conventional
nucleophilic
substitution,
oxirane
opening,
(3+2)‐cycloaddition
(thio)cyano
group
well
their
combinations
realized
telescopic
also
demonstrated.
magnified
image
