Synthesis of Ester-Substituted Polycyclic N-Heteroaromatics via Photocatalyzed Alkoxycarbonylation/Tricyclization Reactions of Enediyne in Continuous Flow Conditions
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 20, 2025
For
the
first
time,
a
photoredox-catalyzed
alkoxycarbonylation/tricyclization
reaction
was
developed
by
employing
readily
accessible
enediynes
and
alkyloxalyl
chlorides
as
starting
materials,
enabling
synthesis
of
ester-substituted
polycyclic
N-heteroaromatics
under
mild
conditions
through
radical-mediated
mechanism.
This
photocatalytic
strategy
is
notable
for
its
exceptional
compatibility
with
diverse
functional
groups,
scalability,
efficiency
in
formation
rings
chemical
bonds.
Notably,
continuous
flow
photocatalysis
technology
markedly
improved
these
reactions
compared
to
equivalent
batch
reactions,
efficiently
decreasing
times
merely
40
min.
Language: Английский
Photoredox/HAT-Catalyzed Intramolecular Hydrocyclization of Alkenes toward 2,3-Fused Quinazolinones and Dihydroquinazolinones
Dong Li,
No information about this author
Xiaoqing Wang,
No information about this author
Yanhui Gou
No information about this author
et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 2, 2024
New
photochemical
approaches
to
2,3-fused
quinazolinones
and
dihydroquinazolinones
are
disclosed.
The
intramolecular
hydrocyclization
proceeds
in
moderate
excellent
yields
across
diverse
alkenes
with
high
regioselectivity
diastereocontrol.
Mechanistic
studies
indicated
that
the
radical
cascade
processes
involve
thiophenol
acting
as
single-electron
transfer
hydrogen
atom
reagents.
success
of
gram-scale
synthesis
proves
strategy
can
be
used
for
practical
applications.
Language: Английский