Base-Promoted Regioselective Annulation of Pyridinium Ylides and Bromoalkynes for the Chemodivergent Synthesis of Indolizines
Xiang Wang,
No information about this author
Huayou Hu,
No information about this author
Qiuyun Li
No information about this author
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 Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 19, 2025
A
straightforward
and
efficient
strategy
for
the
synthesis
of
fully
functionalized
indolizines
has
been
developed
through
a
transition
metal-
oxidant-free
[3
+
2]
cycloaddition
reaction
zwitterionic
ketenimines
pyridinium
salts.
This
versatile
method
proceeds
under
mild
conditions,
affording
in
moderate
to
good
yields.
approach
involves
an
intermolecular
cycloaddition,
followed
by
enamine/imine
tautomerization
aromatization.
Notably,
this
demonstrates
broad
functional
group
compatibility
allows
facile
scalability,
making
it
valuable
tool
indolizine-based
frameworks
organic
medicinal
chemistry.
Language: Английский
Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4H-pyrans
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 27, 2024
A
three-component
annulation
reaction
and
trifluoromethylation
for
the
construction
of
3-(trifluoromethyl)-4
Language: Английский
Recent Advances in the Development of Indolizine Scaffolds: Synthetic Methodology and Mechanistic Insights
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 20, 2024
Comprehensive
Summary
Indolizine
is
a
nitrogen‐containing
heterocycle
with
strong
aromaticity,
possessing
delocalized
10π‐electron
system.
Based
on
the
indolizine
scaffolds,
numerous
molecules
biological
activity
and
organic
functional
materials
have
been
synthesized.
Since
2016,
over
110
papers
published
synthesis
of
but
reviews
synthesizing
scaffolds
incomplete
not
up‐to‐date.
Herein,
from
perspective
structure
combination
pyrrole
pyridine
ring,
we
focus
construction
through
diversity
starting
substrates,
including
derivatives
(N1‐substituted
pyridinium
salt
derivatives,
C2‐substituted
N1‐
C2‐free
substituted
derivatives),
unoriginal
ring
substrates.
Furthermore,
corresponding
reaction
mechanisms
synthetic
methodologies
are
also
elaborated.
Therefore,
this
review
only
paves
way
for
provides
insight
into
exploring
new
modes
constructing
heterocycles.
Key
Scientists
was
discovered
by
Angeli
in
1890
first
prepared
Scholtz
1912
α‐picoline
acetic
anhydride.
A
general
approach
developed
Chichibabin
1927,
that
practical
value
preparation
2‐alkyl‐
or
2‐arylindolizines.
The
closure
quaternary
halides.
At
begining
21st
century,
Basavaiah
introduced
dimension
Baylis‐Hillman
chemistry
leading
to
novel
facile
convenient
methodology
one‐pot
operation.
In
2010,
Barluenga
reported
Cu(I)‐catalyzed
regioselective
[3+2]
cyclization
unsubstituted
pyridines
toward
alkenyldiazoacetates
functionalized
successful
example
metal‐catalyzed
π‐deficient
heterocyclic
system
alkenyldiazo
compounds.
2019
2022,
Xi
Liu
exploited
methods
non‐pyridine
as
synthesize
indolizines,
respectively.
Guo
an
environmentally
benign
electrooxidative
formyl‐
acyl‐substituted
indolizines.
Language: Английский
Intramolecular/Intermolecular Sequential Cyclization Accompanied by Double C–F Bond Cleavage: Access to Tricyclic Fluorine-Containing Pyrano[3,2-c]chromenes
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(22), P. 16553 - 16563
Published: Oct. 28, 2024
Defluorinative
cyclization
of
CF
Language: Английский