Iron(III)-Mediated Nucleophilic Cascade Cyclization of Tertiary Enamides with Diselenides for the Construction of 3-Seleno-2-pyridones
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 12, 2025
An
iron(III)-mediated
nucleophilic
cascade
cyclization
of
N-propiolyl
enamides
with
various
diselenides
was
developed,
which
provides
an
efficient
way
to
construct
seleno-heterocycles.
A
mechanism
study
shows
that
the
process
involves
selective
addition
C≡C
bond
generating
a
seleniranium
ion,
followed
by
intramolecular
attack
enaminic
carbon
tertiary
enamide.
Utilizing
this
protocol,
variety
3-seleno-2-pyridones
were
successfully
synthesized
featuring
good
functional
group
compatibility
and
simple
operation.
Language: Английский
Base-Catalyzed Chalcogenative Annulation of N-Maleimido O-Aminobenzyl Alcohol with Elemental Sulfur/Selenium: Access to 1,4-Sulfa-/Selena-zepanes
Yuanmin Wen,
No information about this author
Teng Liu,
No information about this author
Shuntao Huang
No information about this author
et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 17, 2025
We
reported
an
unprecedented
chalcogen
element
(Se,
S)
insertion
reaction
with
functionalized
aminomaleimide
to
assemble
medium-sized
nitrogen-containing
organic
selenium/sulfur
catalyzed
by
bases.
During
these
[5/6
+
1]
tandem
annulations,
a
variety
of
low-valent
inorganic
chalcogenides
exhibited
excellent
compatibility,
providing
wide
scope
structurally
diverse
1,4-selenazepanes
(17
examples,
60–71%
yields),
1,4-benzothiazepines
(20
74–86%
and
1,4-thiazines
(6
31–68%
yields).
The
characteristics
this
transformation
are
high
atomic
economy,
formation
two
C–Se
or
C–S
bonds
in
one
step,
avoiding
the
use
unstable
toxic
reagents
under
mild
conditions.
Language: Английский