Unveiling the Synthesis of Indole-Fused Eight-Membered Aza-Heterocycles via FeCl3–Catalyzed Radical C–N Coupling and Photophysical Studies
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 25, 2025
A
novel
strategy
toward
construction
of
indole-fused
eight-membered
heterocyclic
rings
through
a
radical
pathway
has
been
reported.
Our
approach
involves
tandem
cyclization
via
FeCl3-catalyzed
cross-dehydrogenative
double
C–N
bond
formation
using
DDQ
as
an
oxidant
under
mild
condition.
An
EPR
experiment
and
time
course
1H
NMR
study
confirm
that
the
addition
triggers
pyrazole
N-radical,
which
contributes
to
eight-member
framework
with
good
yield.
The
structural
diversity
synthetic
utility
have
explored,
along
photophysical
properties
synthesized
compounds.
Language: Английский
Palladium(0)-Catalyzed Regioselective Three-Component Cross-Coupling via C–H Activation: Synthesis of Eight-Membered Azacycles
Qiongqiong Zhu,
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Xiang Zuo,
No information about this author
Cang Cheng
No information about this author
et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 25, 2025
A
Pd(0)-catalyzed
three-component
cross-coupling
reaction
involving
o-bromobenzylamines,
aryl
iodides,
and
alkynes
was
developed
through
C–H
activation.
This
exhibits
excellent
regioselectivity,
selectively
forming
a
C(vinyl)–C(aryl)
bond.
The
process
yields
eight-membered
azacycles
as
the
products,
providing
straightforward
access
to
such
compounds
using
simple
substrates.
Language: Английский
Synthesis of 8-membered trifluoromethyl benzoxazocines via a Pd-catalyzed ring-expansion reaction of trifluoromethyl benzoxazinones with 2-methylidenetrimethylene carbonate and mechanistic investigations
Bo Yang,
No information about this author
Pengfei Sun,
No information about this author
Xue Ma
No information about this author
et al.
Organic Chemistry Frontiers,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
A
Pd-catalyzed
ring-expansion
reaction
of
trifluoromethyl
benzoxazinones
with
2-methylidenetrimethylene
carbonate
to
access
8-membered
benzoxazocines
is
reported.
Language: Английский
Ring opening of donor-acceptor-type cyclopropene unveils electrophilic ketene with vinylogous [4 C + n] periselective cyclization mode
Nature Communications,
Journal Year:
2025,
Volume and Issue:
16(1)
Published: April 29, 2025
Since
its
advent
120
years
ago,
the
[2+n]
coupling
cyclization
of
ketene
has
been
prevalently
used
for
synthesis
N-
and
O-heterocycles.
In
contrast,
vinylogous
version,
i.e.,
use
alkenyl
as
4
C
synthon,
remain
elusive.
We
report
herein
that
in
rare
SN1-type
ring-opening
electron-deficient
cyclopropene,
initially
formed
sp2-carbocation-containing
zwitterionic
intermediate
undergoes
facile
1,4-alkoxy
migration
to
generate
a
functionalized
ketene.
This
electrophilic
not
only
allows
challenging
N-nucleophiles
be
engaged
conventional
reactions
(n
=
1
~
3),
also
unveiled
[4+n]
mode,
exemplified
by
[4
+
1]
formal
4]
construct
pyrrolidinone
azocine
frameworks.
The
protocol
offers
unified
entry
distinct
class
lactam
scaffolds
exhibit
anti-cancer
potential,
constituent
key
natural
product
scaffold
display
interesting
1e-
2e-
reactivities.
work
reveals
broader
synthetic
potential
SN1
type
cyclopropene
"dehydro"-donor-acceptor
cyclopropane
(DDAC)
substrate,
could
have
ramifications
chemistry,
N-heterocyclic
chemistry
related
medicinal
research,
well
donor-acceptor
system
chemistry.
Language: Английский
Lewis Acid-Catalyzed Domino Inverse Electron-Demand Diels–Alder/Thermal Ring Expansion Reaction for the Synthesis of Arene-Annulated Eight-Membered Nitrogen Heterocycles
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 1, 2025
A
domino
inverse
electron-demand
Diels-Alder
reaction/thermal
ring
expansion
sequence
was
developed
to
enable
the
one-step
synthesis
of
arene-annulated
eight-membered
nitrogen
heterocycles
from
readily
available
aromatic
1,2-diazines.
boron-based,
bidentate
Lewis
acid
catalyst
facilitates
initial
cycloaddition
Boc-protected
2-azetine
with
various
electron-poor
and
electron-rich
phthalazines.
The
subsequent
electrocyclic
furnishes
azocines
fused
differently
substituted
aromatics,
a
structural
motif
that
holds
vast
potential
for
further
derivatization.
Language: Английский
Visible Light-Induced Cascade Phosphorylation/Cyclization to Access Phosphorus-Containing Diazocinocarbazoles
Yifan Yin,
No information about this author
Fei Liu,
No information about this author
Miao Tian
No information about this author
et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 16, 2025
Herein,
we
developed
a
novel
radical
cascade
phosphorylation/cyclization
strategy
to
access
phosphorus-containing
diazocine-fused
carbazoles
in
moderate
good
yields,
offering
expanded
opportunities
for
the
exploration
of
biologically
active
molecules.
This
method
features
metal-free
photochemical
tandem,
mild
conditions,
broad
substrate
scopes,
and
scale-up
ability.
Mechanistic
experiments
implied
that
this
photocatalyzed
reaction
was
realized
by
sequence
EnT/SET/SET/radical
addition/cyclization/SET/deprotonation
processes.
Language: Английский
Expedient synthesis of 8-membered azasultams: A combined synthetic, DFT, and in vitro study
Tetrahedron Chem,
Journal Year:
2024,
Volume and Issue:
11, P. 100085 - 100085
Published: July 17, 2024
Language: Английский
Sc(OTf)3-Catalyzed Precise Construction of Medium-Sized [4.2.1]-Oxabridged Scaffolds
Dong-Sheng Ji,
No information about this author
Chenxing Zhou,
No information about this author
Xudong Wang
No information about this author
et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 18, 2024
In
this
study,
the
readily
available
and
inexpensive
Sc(OTf)
Language: Английский
Palladium/Phosphine Complex Catalyzed [4+4] Annulations of Morita-Baylis-Hillman Carbonates and 1-Azadienes
Bo Zhu,
No information about this author
Yang Yang,
No information about this author
Qiang Liu
No information about this author
et al.
Chinese Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
44(12), P. 3761 - 3761
Published: Jan. 1, 2024
Language: Английский
Evaluation of Quinazolin-2,4-Dione Derivatives as Promising Antibacterial Agents: Synthesis, In Vitro, In Silico ADMET and Molecular Docking Approaches
Molecules,
Journal Year:
2024,
Volume and Issue:
29(23), P. 5529 - 5529
Published: Nov. 22, 2024
A
series
of
new
quinazolin-2,4-dione
derivatives
incorporating
amide/eight-membered
nitrogen-heterocycles
2a–c,
in
addition,
acylthiourea/amide/dithiolan-4-one
and/or
phenylthiazolidin-4-one
3a–d
and
4a–d.
The
starting
compound
1
was
prepared
by
reaction
4-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-benzoyl
chloride
with
ammonium
thiocyanate
cyanoacetic
acid
hydrazide.
strong
electrophiles,
namely,
o-aminophenol,
o-amino
thiophenol,
o-phenylene
diamine,
resulted
corresponding
eight-membered
2a–d.
Compounds
4a–d
were
synthesized
good-to-excellent
yield
through
a
one-pot
multi-component
(MCR)
carbon
disulfide
phenyl
isocyanate
under
mild
alkaline
conditions,
followed
ethyl
chloroacetate,
iodide,
methyl
concentrated
HCl,
respectively.
obtained
products
physicochemically
characterized
melting
points,
elemental
analysis,
spectroscopic
techniques,
such
as
FT-IR,
1H-NMR,
13C-NMR,
MS.
antibacterial
efficacy
the
eleven
molecules
examined
vitro
against
two
Gram-positive
bacterial
strains
(Staphylococcus
aureus
Staphylococcus
haemolyticus).
Furthermore,
Computer-Aided
Drug
Design
(CADD)
performed
on
derivatives,
standard
drug
(Methotrexate),
reported
target
enzymes
(S.
S.
haemolyticus)
to
explain
their
binding
mode
actions.
Notably,
our
findings
highlight
compounds
2b
2c
showing
both
best
activity
docking
scores
targets.
Finally,
according
ADMET
predictions,
possessed
acceptable
pharmacokinetics
properties
drug-likeness
properties.
Language: Английский