Base-Promoted Regioselective Annulation of Pyridinium Ylides and Bromoalkynes for the Chemodivergent Synthesis of Indolizines
Xiang Wang,
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Huayou Hu,
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Qiuyun Li
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 5, 2025
A
base-promoted
regioselective
formal
[3
+
2]
annulation
of
pyridinium
ylides
with
bromoalkynes
is
reported,
producing
a
series
substituent-diverse
indolizines
in
generally
good
yields.
mild
K2CO3-promoted
three-component
cyclization
and
at
2:1
molar
ratio
delivered
C2-acylmethylated
indolizines,
whereas
C2-brominated
were
generated
starting
from
bearing
strong
electron-withdrawing
groups
the
unit
by
using
2,2,6,6-tetramethyl-1-piperidinyloxy
as
dehydrogenating
reagent.
The
current
synthetic
methodology
offers
controllable
modular
approach
to
access
different
substitution
patterns,
featuring
wide
substrate
scope,
functional
group
compatibility,
complete
regioselectivity
without
demand
any
transition-metal
catalysts.
Language: Английский
Synthesis of Highly Functionalized Indolizines via NIS-Promoted Spiroannulation/Ring-Opening Aromatization of Alkylidene Oxindoles with 2-(Pyridin-2-yl)acetate Derivatives
Luan-Ting Wu,
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Honglin Diao,
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Yi Wu
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 10, 2025
A
novel
NIS-promoted
domino
reaction
of
alkylidene
oxindoles
with
2-(pyridin-2-yl)acetate
derivatives
has
been
established,
enabling
the
efficient
and
straightforward
synthesis
a
vast
variety
highly
functionalized
indolizines
via
sequential
spiroannulation
ring-opening
aromatization
processes.
The
protocol
features
mild
conditions,
broad
substrate
scope,
high
efficiency,
scalability,
applicability
for
preparation
CF3-containing
indolizines.
Furthermore,
functional
groups
in
indolizine
framework
provide
feasibility
follow-up
derivatization.
Based
on
mechanistic
studies,
plausible
radical
mechanism
is
proposed
to
elucidate
formation
Language: Английский
Domino Approach to Heterocycles-Based Unsymmetrical Triarylmethanes through Heteroannulation of 2-(2-Enynyl)-pyridines with Enaminones
Feroz Ahmad,
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Pavit K. Ranga,
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Shaheen Fatma
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et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(17), P. 12104 - 12117
Published: Aug. 13, 2024
Herein,
we
report
a
copper-catalyzed
protocol
to
access
unsymmetrical
triarylmethanes
containing
both
indolizine
and
the
chromone
scaffolds
in
same
molecule
via
5-endo-dig
cyclization
of
2-(2-enynyl)-pyridines
followed
by
reaction
with
2-hydroxyaryl
enaminones.
A
variety
enaminones
were
subjected
under
optimal
conditions,
respective
obtained
good
excellent
yields.
Language: Английский
Silver(I)-Promoted [3 + 3]-Cycloaddition of 2-(2-Enynyl)quinolines with N′-(2-Alkynylbenzylidene)hydrazides
Feng Li,
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Qing Yang,
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He Li
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et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(16), P. 11567 - 11575
Published: Aug. 1, 2024
An
effective
and
straightforward
Ag(I)-mediated
annulation
of
2-(2-enynyl)quinolines
N'-(2-alkynylbenzylidene)hydrazides
was
developed,
forging
various
synthetically
challenging
17bH-isoquinolino[2'',1'':1′,6']pyridazino[4′,5′:3,4]pyrrolo[1,2-a]quinolines,
including
different
nitrogen-containing
fused
rings,
in
moderate
to
excellent
yields.
This
one-pot
cycloaddition
strategy
features
exclusive
regioselectivity,
high
atom
economy,
broad
substrate
scope
under
mild
conditions.
The
practicality
reliability
this
reaction
demonstrated
by
a
successful
scale-up
synthesis.
Language: Английский