Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
366(1), P. 141 - 147
Published: Nov. 28, 2023
Abstract
Presented
herein
is
a
synthesis
of
indane
fused
bicyclic
pyrazolidinones
based
on
the
reactions
aryl
azomethine
imines
with
cyclopropanols.
Mechanistically,
formation
product
involves
Rh(III)‐catalyzed
direct
C(
sp
2
)−H
alkylation
imine
cyclopropanol
through
in
situ
ring‐opening,
followed
by
cascade
intramolecular
C
‐
and
N
‐nucleophilic
addition.
In
this
tandem
process,
acts
as
not
only
an
alkylating
agent
but
also
masked
nucleophile
electrophile
to
participate
construction
both
pyrazolidinone
scaffolds.
To
our
knowledge,
such
reaction
pattern
has
been
disclosed.
general,
synthetic
protocol
advantages
easily
obtainable
substrates,
valuable
products,
concise
procedure,
unique
pathway,
good
compatibility
diverse
functional
groups.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(29)
Published: March 31, 2023
Abstract
Benzothiophenes,
activated
by
oxidation
to
the
corresponding
S
‐oxides,
undergo
C−H/C−H‐type
coupling
with
phenols
give
C4
arylation
products.
While
an
electron‐withdrawing
group
at
C3
of
benzothiophene
is
important,
process
operates
without
a
directing
and
metal
catalyst,
thus
rendering
it
compatible
sensitive
functionalities—e.g.
halides
formyl
groups.
Quantum
chemical
calculations
suggest
formal
stepwise
mechanism
involving
heterolytic
cleavage
aryloxysulfur
species
π‐complex
phenoxonium
cation.
Subsequent
addition
cation
position
favored
over
C3;
Fukui
functions
predict
that
major
regioisomer
formed
more
electron‐rich
between
C4.
Varied
selective
manipulation
products
showcase
synthetic
utility
metal‐free
process.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(19), P. 4941 - 4971
Published: Jan. 1, 2023
A
summary
of
the
various
ring
opening
reactions
strained
and
unstrained
cycloalkanols
is
elaborated
in
present
review.
Key
emphasis
on
reactivities
pertaining
to
cyclopropanols,
cyclobutanols
higher
analogues
provided.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(12), P. 2058 - 2062
Published: March 17, 2023
A
Fe(NO3)3-mediated
ring-opening
arylation
of
cyclopropanol
with
the
electron-rich
pyrrole
has
been
developed,
which
might
proceed
through
oxidative
radical
ring
opening
followed
by
cyclization
to
motif
and
then
aromatization.
This
method
enables
direct
without
prefunctionalization
thus
allows
rapid
access
a
diverse
array
chiral
5,6,7,8-tetrahydroindolizines
from
easily
available
amino
acid
esters.
The
synthetic
utility
demonstrated
asymmetric
synthesis
alklaoids
(-)-indolizidine
167B,
(+)-indolizidine
209D,
(+)-monomorine
I,
natural
product
analogue.
Synthesis,
Journal Year:
2023,
Volume and Issue:
55(21), P. 3454 - 3469
Published: March 20, 2023
Abstract
C8-Substituted
quinoline
(QN)
and
1,2,3,4-tetrahydroquinoline
(THQ)
scaffolds
are
featured
in
numerous
bioactive
compounds
natural
products.
Appreciable
efforts
have
been
made
towards
the
development
of
elegant
techniques
to
functionalize
C8–H
bond
QNs
THQs.
The
transition-metal-catalyzed
chelation-assisted
C–H
activation
strategy
has
emerged
as
an
effective
synthetic
tool
among
existing
methods.
This
review
focuses
on
recent
advances
directed
carbon–carbon
forming
reactions
for
functionalization
THQs
(till
February
2023).
discussion
categorized
based
type
reaction.
1
Introduction
2
Acylation
3
Alkylation
4
Alkenylation
5
Alkynylation
6
Allylation
7
Annulation
8
Arylation
9
Conclusion
Outlook
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(5)
Published: April 13, 2023
Abstract
A
zinc‐mediated
annulation
reaction
between
cyclopropanols
and
alkylidenemalononitriles
is
reported.
The
promoted
in
the
presence
of
Et
2
Zn
1,4‐diazabicyclo[2.2.2]octane
(DABCO)
DMSO
at
80
°C,
affording
cyclopropane‐fused
6‐amino‐3,4‐dihydro‐2
H
‐pyran‐5‐carbonitrile
derivatives
moderate
to
good
yields
with
high
diastereoselectivity.
proposed
involve
an
enolized
homoenolate
as
key
reactive
intermediate,
which
generated
through
ring
opening
zinc
cyclopropoxide
enolization
resulting
homoenolate.
enolate
moiety
this
species
undergoes
Michael
addition
alkylidenemalononitrile,
followed
by
closure
α‐functionalized
intramolecular
cyclization
one
cyano
groups.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(43), P. 7805 - 7809
Published: Oct. 23, 2023
The
site-selective
C8-alkylation
of
quinolines
has
been
accomplished
using
cyclopropyl
alcohols
as
the
alkylating
agents
and
N-oxide
a
weak
chelating
group
in
presence
Co(III)
catalysis
via
merging
C-H/C-C
bond
activation.
use
cyclopropanol
alkyl
source,
Co
catalysis,
substrate
scope,
HRMS
analysis
reaction
intermediate,
late-stage
mutation
drug
molecules/natural
products
are
important
practical
features.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
21(4), P. 775 - 782
Published: Dec. 19, 2022
A
rhodium-catalyzed
formal
[4
+
1]-cyclization
reaction
of
aryl
substituted
pyrazoles
with
cyclopropanols
via
C-H
bond
activation/cyclization
processes
to
selectively
construct
a
series
carbonyl
functionalized
pyrazolo[5,1-a]isoindoles
is
described.
The
features
good
functional
group
compatibility
and
broad
substrate
scope
respect
both
cyclization
components
up
84%
yields.
Mechanistic
studies
indicated
that
the
cleavage
might
be
rate-determining
step
in
this
transformation.
