Organic Letters,
Год журнала:
2024,
Номер
26(50), С. 10951 - 10957
Опубликована: Дек. 10, 2024
Molecular
editing
of
quinazolinones
to
isoquinolines
by
a
novel
ruthenium-catalyzed
[4+2]
annulation
with
sulfoxonium
ylides
has
been
developed.
The
method
permits
the
precise
and
rapid
assembly
multisubstituted
aminoisoquinolines,
class
heterocycles
that
play
privileged
role
in
organic
synthesis
pharmaceutical
development.
This
new
catalytic
process
exhibits
programmability,
including
directed
C–H
acetylation,
nucleophilic
cyclization,
alcoholysis.
Remarkably,
various
2-arylquinazolinones
could
be
employed
excellent
yields
broad
functional
group
tolerance.
heterocycle-to-heterocycle
protocol
is
compatible
green
chemistry
using
an
EtOH
solvent
releasing
H2O
dimethyl
sulfoxide
as
byproducts.
Organic Chemistry Frontiers,
Год журнала:
2017,
Номер
5(6), С. 998 - 1002
Опубликована: Дек. 22, 2017
Sulfoxonium
ylides
acts
as
a
bifunctional
C2-synthon
in
Rh(iii)-catalyzed
redox-neutral
annulative
coupling
with
arenes
for
the
synthesis
of
N-heterocycles
and
carbocycles.
ACS Catalysis,
Год журнала:
2020,
Номер
10(17), С. 9747 - 9757
Опубликована: Авг. 3, 2020
Transition-metal-catalyzed
C–H
activation
followed
by
oxidative
cyclization
with
unsaturated
coupling
partners
has
been
a
valuable
synthetic
tool
for
the
multiring
molecular
scaffolds.
This
Perspective
introduces
recent
progress
on
Cp*M-catalyzed
(M
=
Co,
Rh,
and
Ir)
direct
annulation
of
functionalized
arenes
terminal
alkynes
their
equivalents
through
bond
cleavage.
The
highlighted
examples
are
categorized
according
to
10
different
types
reagents
used
in
transformations.
representative
conditions,
selected
reaction
scope,
key
mechanistic
aspects
briefly
summarized.
Organic Chemistry Frontiers,
Год журнала:
2019,
Номер
6(13), С. 2120 - 2141
Опубликована: Янв. 1, 2019
This
review
focuses
on
the
synthesis
of
N-heterocycles
using
amidines
as
starting
materials,
with
an
emphasis
mechanisms
these
reactionsviaC–N/C–C
bond
formation.
Journal of the American Chemical Society,
Год журнала:
2018,
Номер
141(1), С. 98 - 103
Опубликована: Дек. 18, 2018
The
reaction
of
various
organozinc
pivalates
with
anthranils
provides
anilines
derivatives,
which
cyclize
under
acidic
conditions
providing
condensed
quinolines.
Using
alkenylzinc
pivalates,
electron-rich
arylzinc
or
heterocyclic
zinc
produces
directly
the
quinolines
several
structures
belong
to
new
scaffolds.
These
N-heterocycles
are
particular
interest
for
organic
light
emitting
diodes
their
high
photoluminescence
quantum
yields
and
long
exciton
lifetimes
as
well
hole-transporting
materials
in
methylammonium
lead
iodide
perovskites
solar
cells
due
an
optimal
band
alignment
holes
a
large
bandgap.
Advanced Synthesis & Catalysis,
Год журнала:
2018,
Номер
360(21), С. 4049 - 4053
Опубликована: Авг. 20, 2018
Abstract
A
ruthenium‐catalyzed
direct
mono‐C−H
functionalization/annulation
cascade
reaction
of
benzimidates
and
sulfoxonium
ylides
has
been
developed.
The
proceeds
smoothly
with
a
broad
range
substrates,
giving
access
to
variety
isoquinoline
derivatives
in
moderate
good
yields
using
an
organic
acid
additive
under
oxidant
free
conditions.
magnified
image
Asian Journal of Organic Chemistry,
Год журнала:
2018,
Номер
7(7), С. 1217 - 1235
Опубликована: Май 30, 2018
Abstract
Electron‐deficient
aromatic
heterocycles,
such
as
pyridine,
quinoline,
and
isoquinoline,
occupy
a
vast
rapidly
expanding
area
of
chemistry
because
the
obvious
application
their
derivatives
in
medicine,
agriculture,
polymers,
other
fields.
These
heterocycles
are
rather
poorly
reactive
towards
electrophilic
metalation
by
C−H
activation
oxidative
mechanisms.
The
catalytic
functionalization
electron‐
deficient
remains
challenge
for
synthetic
community.
This
Focus
Review
highlights
significant
developments
made
transition‐metal‐catalyzed
π‐deficient
heterocycles.
Organic Letters,
Год журнала:
2018,
Номер
20(23), С. 7645 - 7649
Опубликована: Ноя. 20, 2018
In
the
present
study,
a
novel
synthetic
strategy
to
directly
produce
versatile
3-acylindoles
through
Rh(III)-catalyzed
C-H
activation
and
annulation
cascade
of
N-phenylamidines
with
α-Cl
ketones
was
developed,
in
which
serve
as
unusual
one-carbon
(sp3)
synthons.
This
features
high
regioselectivity,
efficiency,
wide
substrate
tolerance,
mild
reaction
conditions,
further
underscore
its
utility
drug
molecule
synthesis.
The Journal of Organic Chemistry,
Год журнала:
2018,
Номер
83(21), С. 13463 - 13472
Опубликована: Окт. 9, 2018
A
simple
C–H/N–H
bond
functionalization
of
N-aryl
amidines
with
cyclic
2-diazo-1,3-diketones
for
the
synthesis
1-aminoisoquinolines
has
been
accomplished
by
employing
[Cp*RhCl2]2/CsOPiv
as
catalyst
system.
This
methodology
proceeds
a
cascade
C–H
activation/intramolecular
cyclization
under
mild
reaction
conditions,
features
broad
substrate
scope,
and
involves
formation
two
new
σ
bonds
(C–C
C–N)
in
single
operation
construction
novel
1-aminoisoquinoline
skeletons
good
to
excellent
yields.
