Scientia Sinica Chimica,
Journal Year:
2023,
Volume and Issue:
53(9), P. 1735 - 1740
Published: June 27, 2023
The
direct
functionalization
of
C–H
bonds
has
become
an
efficient
method
for
constructing
carbon–carbon
in
organic
synthesis.
As
the
transformation
does
not
require
pre-functionalization,
it
is
regarded
as
atom-economic
and
step-economic
method.
The
transition
metal
catalyzed
selective
provides
a
concise
construction
C–C
C–X
bonds.
Although
Rh(III)-catalyzed
ring-opening
reactions
azabenzonorbornadienes
via
activation
have
been
studied,
usually
addition
oxidant
or
harsh
reaction
conditions.
Herein,
we
develop
with
2-arylindole,
which
oxidants,
featured
by
high
regioselectivity
stereoselectivity
good
functional
group
compatibility.
yield
up
to
98%
under
mild
condition,
thus
convenient
synthesis
2-aryl
hydrogenaphthalene
derivatives.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(1), P. 62 - 67
Published: Jan. 3, 2024
We
have
found
a
chameleonic
reactivity
of
imidoyl
sulfoxonium
ylides.
On
the
one
hand,
ylides
react
with
electron-deficient
reagents,
such
as
alkynyl
esters,
to
lead
formation
1,2-dihydro-pyridines.
The
methyl
group
attached
sulfur
atom
acts
methylene
donor.
other
pyridinium
1,4-zwitterionic
thiolates,
which
leads
functionalized
pyrroles.
Both
transformations
feature
mild
reaction
conditions
and
good
functional
tolerance.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
90(4), P. 1663 - 1670
Published: Jan. 21, 2025
1H-Isochromene
scaffolds
are
ubiquitous
in
natural
products
and
significant
bioactive
molecules.
Although
several
methods
for
these
molecular
syntheses
have
been
developed,
reports
on
the
efficient
construction
of
iminated
isochromenes
still
rather
limited.
Herein,
we
report
a
new
Cu(II)-catalyzed
annulation
sulfonylimination
cascade
α-carbonyl-γ-alkynyl
sulfoxonium
ylides
with
sulfamides,
enabling
direct
C-C
σ-bond
elimination
to
furnish
(Z)-1H-isochromenes
51-97%
yields.
During
reaction
process,
ylide
unit
as
traceless
eliminative
group
is
key
successful
sulfonylimination,
which
enables
N-H
insertion
subsequent
acetic
acid-mediated
elimination.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(3), P. 1898 - 1906
Published: Jan. 17, 2023
A
new
efficient
and
stereoselective
synthesis
of
12-tetrazolyl
substituted
(E)-5H-quinazolino[3,2-a]quinazolines
via
sequential
Ugi-azide/Staudinger/aza-Wittig/addition/Ag(I)-catalyzed
cyclization
was
developed.
The
four-component
reactions
2-azidobenzaldehyde,
2-(alkynyl)benzenamine,
isocyanide,
trimethylsilyl
azide
gave
Ugi-azide
intermediates,
which
were
subsequently
treated
with
triphenylphosphine
isocyanate
to
produce
in
the
presence
Ag(I)
catalyst
K2CO3.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(11), P. 2557 - 2564
Published: March 22, 2024
Abstract
An
iodine/DMSO‐promoted
approach
has
been
developed
for
the
synthesis
of
indoloquinolines
via
a
sequential
sp
3
C−H
oxidation/intramolecular
cyclization
using
2‐(1
H
‐indol‐2‐yl)anilines
and
aryl
methyl
ketones.
A
wide
range
ketones,
including
drugs
complex
bioactive
molecule‐derived
substrates
were
compatible
in
present
reaction
with
yields
30–96%.
This
protocol
proceeds
through
oxidation
ketones
to
phenylglyoxals,
subsequent
imine
formation,
furnish
indoloquinolines.
Further,
is
applicable
gram‐scale
operationally
simple.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(17), P. 12204 - 12227
Published: Aug. 9, 2024
Herein,
a
straightforward
facile
synthesis
of
indolo[2,3-c]quinoline
analogues
was
reported
from
2-arylamino(phenylsulfonyl)methylindoles
involving
PIDA/BF3·OEt2-mediated
intramolecular
dehydrogenative
coupling
(IDC)
as
key
step.
Even
though
isomeric
3-arylamino(phenylsulfonyl)methylindoles,
upon
interaction
with
PIDA/BF3·OEt2,
led
to
complications,
the
indolo[3,2-c]quinoline
framework
could
be
easily
achieved
N-(2-iodoaryl)-N-indolylmethylbenzenesulfonamide
by
employing
Pd(0)-mediated
cyclization
reaction.
Under
identical
conditions,
indolo[2,3-c]quinolines
also
accomplished
respective
N-(2-iodoaryl)-N-indolylmethylbenzenesulfonamides.
The
SRB
assay
fluorine-bound
indoloquinolines
displayed
nanomolar-level
cytotoxicity
against
nonsmall
lung
cancer
cell
line,
NCI-H460.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(13), P. 8781 - 8790
Published: June 5, 2023
Reactions
involving
C(sp3)-H
bonds
of
azaarenes
have
been
widely
studied
in
recent
years
as
they
allow
direct
functionalization
these
N-heterocycles
without
the
use
harsh
reaction
conditions.
In
this
work,
we
describe
4-methylquinazolines
and
1-benzylisoquinolines,
employing
α-substituted
β-nitrostyrenes
catalyzed
by
inexpensive
copper
acetate.
Under
optimized
condition,
21
pyrrolo[1,2-c]quinazolines,
well
an
imidazo[1,2-c]quinazoline
4
pyrrolo[2,1-a]isoquinolines,
were
obtained
moderate
to
good
yields.
Furthermore,
biological
activity
pyrrolo[1,2-c]quinazolines
was
evaluated
against
Plasmodium
falciparum,
promising
results
obtained.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(31), P. 6342 - 6351
Published: Jan. 1, 2024
A
facile
strategy
for
the
synthesis
of
valuable
indolines
has
been
developed,
involving
a
palladium(II)/Brønsted
acid
co-catalyzed
annulation
readily
available
(2-aminophenyl)methanols
and
sulfoxonium
ylides.
This
protocol
allows
direct
utilization
OH
group
as
leaving
group,
tolerates
alkyl
aryl
groups
on
N
atom
aniline
moiety,
operates
under
mild
reaction
conditions,
exhibits
good
efficiency.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 27, 2024
A
metal-free
approach
for
synthesizing
hybrid
quinoxaline
derivatives
from
sulfoxonium
ylide
and
a
1,5-bis-nucleophilic
N-heterocycle
mediated
by
elemental
sulfur
is
presented
to
illuminate
the
[5+1]
cascade
cyclization
sequence.
Large-scale
synthesis
postsynthetic
functionalizations
annulative
π-extension
intramolecular
aza-annulation
reactions
reveal
potential
utility
actualize
fabricated
approach.
