Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 10, 2024
Comprehensive
Summary
Two
reaction
modes
for
metal‐free
[3
+
2]
cyclization
of
N
‐aminopyridinium
derivatives
with
β
‐alkoxyvinyl
trifluoromethylketones
have
been
described
through
selective
C—O
or
C—O/C—C
bond
cleavage.
This
strategy
can
also
be
extended
to
the
enaminones
and
bromoalkynes.
A
broad
range
‐aminopyridinium,
‐aminoquinolinium,
‐aminoisoquinolinium
salts
are
well
tolerated,
enabling
divergent
synthesis
trifluoroacylated,
non‐substituted,
acylated,
brominated
pyrazolo[1,5‐
a
]pyridine
(62
examples).
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(22), P. 5717 - 5734
Published: Jan. 1, 2023
Vinylene
carbonate
(VC)
has
emerged
as
a
promising
coupling
partner
to
participate
in
various
attractive
C–H
conversions
and
implement
an
increasing
number
of
novel
reactions.
In
this
review,
we
provide
summary
the
advancements
achieved
metal-catalyzed
functionalization
using
VC.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(12), P. 2892 - 2897
Published: Jan. 1, 2023
By
utilizing
the
dual
reactivity
function
of
N
-aminopyridinium
ylides,
we
developed
a
direct
[3
+
2]-cycloaddition
ylides
and
ynals
to
build
pyrazolo[1,5-
]pyridine
core
while
introducing
cyano
group.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(48), P. 9604 - 9608
Published: Jan. 1, 2022
An
efficient
metal-free
annulative
vinylene
transfer
protocol
for
the
synthesis
of
benzo-fused
indolizines
via
1,3-dipolar
cycloadditions
N-ylides
with
carbonate
has
been
developed.
Vinylene
serves
as
an
acetylene
surrogate
without
any
external
oxidant
involved.
This
transformation
leads
to
direct
construction
versatile
indolizine
derivatives
in
moderate
good
yields.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(11), P. 7199 - 7207
Published: May 12, 2023
Pyridinium
1,4-zwitterionic
thiolates
were
regarded
as
powerful
and
versatile
building
blocks
to
prepare
nitrogen-
sulfur-containing
heterocycles.
Herein,
we
reported
a
copper-catalyzed
formal
[4
+
1]
annulation
of
pyridinium
diazo
compounds
without
any
additives
access
library
trifunctionalized
indolizines
in
good
yields.
Besides,
isoquinolinium
imidazolium
also
applied
this
reaction.
Of
particular
note
is
that
various
functional
groups
such
-CO2R,
-CO2NR2,
-CF3,
-CN,
-(O)P(OR)2
could
be
easily
introduced
into
cycloaddition
products
by
strategy.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(20), P. 3400 - 3412
Published: Sept. 6, 2023
Abstract
Recently,
vinylene
carbonate
has
been
developed
as
a
powerful
synthon
in
transition
metal‐catalyzed
C−H
bond
activation/cyclization
reactions.
This
review
introduces
recent
progress
the
use
of
reactant,
by
analyzing
and
comparing
reaction
models
involving
surrogate
ethynol,
acetylene,
acetylation
reagents
or
other
reactants,
while
addressing
related
mechanisms
synthetic
applications.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(9), P. 2003 - 2007
Published: March 12, 2024
Abstract
A
DBU‐promoted
[3+2]
cyclization/retro‐Mannich
cascade
reaction
of
N
‐aminoisoquinolinium
and
‐aminoquinolinium
derivatives
with
para
‐quinone
methides
has
been
established,
employing
a
C=C
double
bond
cleavage.
broad
range
salts,
are
well
tolerated,
providing
the
corresponding
rearrangement
products.
Moreover,
scaled‐up
reactions
diverse
derivatizations
products
were
also
investigated
discussed.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(45), P. 9648 - 9653
Published: Nov. 1, 2024
An
unprecedented
five-component
[2
+
2
1
1]
benzannulation
strategy
for
regioselective
assembly
of
densely
functionalized
aromatic
amines
from
two
ynals,
malononitriles,
and
sodium
sulfinates
is
established.
The
protocol
enables
the
efficient
installation
five
substituents
on
a
benzene
ring
via
formation
multiple
chemical
bonds
in
single
operation,
providing
various
multifunctionalized
primary
moderate
to
good
yields.
Additionally,
three-component
[3
cycloaddition
NH4SCN
was
also
achieved
produce
2-amnopyridine
derivatives
with
serving
as
an
ammonia
surrogate.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(23), P. 16655 - 16660
Published: Nov. 14, 2023
A
base-mediated
1,1-difunctionalization
of
vinylene
carbonate
has
been
achieved
using
two
different
nucleophiles,
namely,
thiol
and
alcohol,
with
the
assistance
air
(O2).
In
alcoholic
solvents,
decarboxylation
occurs
at
room
temperature
to
provide
a
1,1-difunctionalized
product,
where
serves
as
an
ethynol
(C2)
synthon
in
this
three-component
reaction.
On
other
hand,
acetonitrile,
exclusive
hydrothiolation
under
basic
conditions
temperature.
This
method
offers
one-pot
decarboxylative
regioselective
difunctionalization
for
construction
α-alkoxy-β-hydroxy
sulfide.
