Abstract
An
intermolecular
copper
catalyzed
heteroannelation
reaction
using
Csp
3
‐Csp
radical
coupling
approach
has
been
accomplished
to
synthesize
2,5‐diphenyl‐3‐(pyrimidin‐2‐yl)‐3,4‐dihydro‐2
H
‐pyrrolo[2,3‐
d
]thiazole.
C−C
between
4‐thiazolidinones
and
O‐acetyl
oximes
under
Cu
catalyst
further
cyclizes
get
the
target
molecule
thiazolidine‐fused
nucleus.
This
unified
method
offers
access
novel
fused
heterocycles
with
pyrimidines
bearing
4‐thiazolidinone
in
moderate
higher
yields.
The
optimization
study
includes
various
catalysts,
oxidants,
bases
solvents
at
different
temperatures.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(10), С. 2502 - 2528
Опубликована: Март 25, 2021
Abstract
Oximes
represent
one
of
the
fundamental
organic
compound
classes
with
a
wide
range
synthetic
applications.
In
last
decade
O
‐substituted
oximes
were
recognized
as
synthetically
available
and
versatile
precursors
iminyl
radicals
via
one‐electron
oxidation
or
reduction
employing
visible
light
photoredox
catalysts,
salts
abundant
metals
(such
Cu
Fe),
other
convenient
reagents.
Iminyl
are
powerful
synthons
for
various
processes
cyclization,
ring‐opening,
CH‐functionalization,
coupling.
The
present
review
is
focused
on
methods
based
oxime‐derived
developed
in
few
years
excluding
ring
opening
reactions
cyclic
that
summarized
recent
publications.
consists
two
main
parts:
(1)
involving
1,n‐hydrogen
atom
transfer
(n=5
most
cases)
(2)
addition
radical
to
carbon‐carbon
π‐bond.
magnified
image
Organic Letters,
Год журнала:
2023,
Номер
25(5), С. 838 - 842
Опубликована: Янв. 27, 2023
A
copper-catalyzed
annulation
of
O-acyl
oximes
with
cyclic
1,3-diones
has
been
developed
for
the
concise
synthesis
7,8-dihydroindolizin-5(6H)-ones
and
cyclohexanone-fused
furans
through
substituent-controlled
selective
radical
coupling
process.
2-Alkyl
undergo
C-C
coupling,
while
2-unsubstituted
C-O
coupling.
Molecules,
Год журнала:
2023,
Номер
28(4), С. 1775 - 1775
Опубликована: Фев. 13, 2023
Oximes
and
hydroxylamines
are
a
very
important
class
of
skeletons
that
not
only
widely
exist
in
natural
products
drug
molecules,
but
also
synthon,
which
have
been
used
industrial
production.
Due
to
weak
N-O
σ
bonds
oximes
hydroxylamines,
they
can
be
easily
transformed
into
other
functional
groups
by
bond
cleavage.
Therefore,
the
synthesis
N-heterocycle
using
as
nitrogen
sources
has
attracted
wide
attention.
Recent
advances
for
through
transition-metal-catalyzed
radical-mediated
cyclization
classified
type
rings
summarized.
In
this
paper,
recent
cleavage
reviewed.
We
hope
review
provides
new
perspective
on
field,
reference
develop
environmentally
friendly
sustainable
methods.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(11)
Опубликована: Янв. 20, 2024
Abstract
A
practical
and
mild
electrochemical
dehydrogenative
regioselective
cyclization
method
has
been
established
for
the
synthesis
of
4‐pyrrolin‐2‐ones
using
3‐aza‐1,5‐dienes
1,3‐dicarbonyl
compounds
as
substrates.
This
protocol
is
catalyst‐free,
metal‐free,
does
not
require
oxidizing
agents.
It
exhibits
wide
substrate
compatibility
can
be
easily
scaled
up
to
gram
scale.
Organic Chemistry Frontiers,
Год журнала:
2020,
Номер
7(15), С. 2107 - 2144
Опубликована: Янв. 1, 2020
This
review
focuses
on
the
recent
advances
in
one-electron
oxidation
involved
oxidative
dehydrogenative
annulations
and
cyclizations
for
intermolecular
intramolecular
construction
of
valuable
ring
structures.
Organic Letters,
Год журнала:
2022,
Номер
24(21), С. 3828 - 3833
Опубликована: Май 23, 2022
A
copper-catalyzed
annulation
of
α,β-unsaturated
O-acyl
ketoximes
with
isoquinolinium
N-ylides
has
been
developed
for
the
concise
synthesis
stable
N-H
imines
a
benzo[7,8]indolizine
core.
When
β-(2-bromoaryl)-α,β-unsaturated
are
used
as
starting
materials,
cascade
cyclization
occurs
to
afford
benzo[7,8]indolizino[1,2-c]quinolines.
Chemical Communications,
Год журнала:
2023,
Номер
59(39), С. 5902 - 5905
Опубликована: Янв. 1, 2023
The
chiral
phosphoric
acid-catalyzed
asymmetric
intermolecular
formal
[3+2]
cycloaddition
of
azoalkenes
with
azlactones
has
been
established.
This
convergent
protocol
leads
to
a
facile
and
enantioselective
de
novo
construction
wide
range
fully
substituted
4-pyrrolin-2-ones
bearing
carbon
atom
in
good
yields
excellent
enantioselectivities
(26
examples,
72-95%
87-99%
ee).
