Silver-catalyzed synthesis of nitrogen heterocycles: recent advancements
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(21), С. 4332 - 4357
Опубликована: Янв. 1, 2023
Silver
catalysis
offers
environmentally
friendly
and
simple
protocols
to
construct
N-heterocycles.
Inspired
by
its
appeal,
herein
we
have
summarized
developments
in
the
silver-catalyzed
synthesis
of
N-heterocycles
since
2019.
Язык: Английский
Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 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.
Язык: Английский
Ag(I)-Mediated Annulation of 2-(2-Enynyl)pyridines and Propargyl Amines to Access 1-(2H-Pyrrol-3-yl)indolizines
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(1), С. 304 - 312
Опубликована: Дек. 21, 2023
An
effective
Ag(I)-mediated
annulation
of
2-(2-enynyl)pyridines
and
propargyl
amines
was
developed,
unexpectedly
affording
a
broad
range
functionalized
1-(2H-pyrrol-3-yl)indolizines
in
moderate
to
excellent
yields.
The
developed
method
is
characterized
by
operational
simplicity,
ready
availability
starting
materials,
high
regioselectivity,
substrate
scope
under
mild
reaction
conditions.
Ag(I)-promoted
cyclization
possibly
results
the
formation
spiroindolizine,
ring-opening
rearrangement
which
may
give
1-(2H-pyrrol-3-yl)indolizine.
Furthermore,
gram-scale
synthetic
transformations
are
also
studied.
Язык: Английский
Metal/catalyst/alkyne/alkene‐free one‐pot synthesis of indolizines from 2‐(pyridin‐2‐yl)acetate, DMF‐DMA and α‐halomethylenes
Journal of Heterocyclic Chemistry,
Год журнала:
2023,
Номер
60(5), С. 825 - 833
Опубликована: Фев. 9, 2023
Abstract
We
have
described
a
simple
and
robust
one‐pot
synthesis
of
1,3‐disubstitued‐indolizines
from
2‐(pyridin‐2‐yl)acetate,
DMF‐DMA
α‐halomethylenes
without
using
metal/catalyst/alkyne/alkene.
This
protocol
provides
variety
indolizine
analogs
via
in‐situ
formed
3‐(dimethylamino)‐2‐(pyridin‐2‐yl)acrylate
intermediate,
undergoes
N‐alkylation
followed
by
Michael
addition/cyclization.
The
gram
scale
developed
this
does
not
require
chromatographic
purification.
post
application
alkyne
bearing
provided
triazole
beta‐ketoester
containing
indolizine‐tethered
pyrimidine
heterocyclic
system.
Язык: Английский
Organocatalyzed Double C(sp3)−H Alkylation of Cyclic N‐Sulfonyl Ketimines with 3‐Chloropropiophenones: Selective Access to 2,3,6‐Trisubstituted Pyridines
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(33)
Опубликована: Июль 11, 2023
Abstract
An
efficient
sequential
one‐pot,
two‐step
pseudo‐four‐component
reaction
between
3/4‐methyl
N
‐sulfonyl
ketimines
with
3‐chloropropiophenones
triggered
by
DIPEA/NaHCO
3
as
a
cooperative
base
and
subsequent
aza‐cyclization
using
NH
4
OAc
is
reported.
This
transition‐metal‐oxidant‐free
technique
concocts
new
C−C/C=C/C=N−C
bonds
selectively,
guaranteeing
acceptable
yields
of
2,3,6‐trisubstituted
pyridines
possessing
ortho
‐hydroxyaryl/benzenesulfonamide
propiophenone
moieties
at
C2
C3
positions,
respectively.
Interestingly,
while
replacing
methyl‐substituents
straight
alkyl
chains
ketimines,
only
monoalkylation
happened
in
situ‐generated
vinyl
ketones
to
deliver
promising
3‐picoline
derivatives.
Moreover,
the
synthetic
transmutation
prepared
pyridine
derivative
led
several
important
classes
pyridocoumarin,
5
H
‐chromenopyridine,
di(pyridin‐3‐yl)
methane
Язык: Английский
Gold-catalyzed intermolecular tandem cyclization/[4 + 3] cycloaddition of 2-(1-alkynyl)-cyclopropyl pyridines with nitrones: an efficient strategy for the synthesis of [1,2]oxazepino[5,4-a] indolizines
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(13), С. 3685 - 3691
Опубликована: Янв. 1, 2024
A
new
method
for
the
synthesis
of
seven-membered
heterocycle-fused
indolizine
scaffolds
from
2-(1-alkynyl-cyclopropyl)pyridines
and
nitrones
under
catalysis
PPh
3
AuNTf
2
.
Язык: Английский
Silver(I)-Promoted [3 + 3]-Cycloaddition of 2-(2-Enynyl)quinolines with N′-(2-Alkynylbenzylidene)hydrazides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(16), С. 11567 - 11575
Опубликована: Авг. 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.
Язык: Английский