Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 25, 2024
A
general
protocol
for
the
synthesis
of
a
variety
functionalized
quinazolinones
has
been
developed
through
sequential
Pd-catalyzed
coupling/1,5-alkyloxy/thio/azole
shift/6π
electrocyclization
reaction
isocyanides
and
2-carbonylaryl
azides.
When
3-(2-isocyanoethyl)indoles
were
utilized,
an
unusual
competitive
between
[1,5]-shift
indole-spirocyclization
was
observed,
which
renders
modular
spiroindolenine-3,3'-pyrrolo[2,1-
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(4), P. 2190 - 2199
Published: Jan. 27, 2024
Ketenimines
represent
an
important
class
of
reactive
species,
useful
synthetic
intermediates,
and
synthons.
However,
in
general,
ketenimines
preferentially
undergoes
nucleophilic
addition
reactions
with
hydroxyl
amino
groups,
carbon
functional
groups
remain
a
less
studied
subset
such
systems.
Herein,
we
develop
straightforward
syntheses
pyridin-4(1H)-imines
that
is
achieved
by
cyclization
reacting
enaminone
unit
α-acylketenimine
which
generated
from
the
sulfonyl
azides
terminal
ynones
situ
(CuAAC/Ring
cleavage
reaction).
The
cascade
process
starts
α-C
instead
group,
attacking
electron-deficient
central
ketenimine,
chemoselectivity
unconventional
products
were
formed
intramolecular
cyclization.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(7), P. 926 - 947
Published: Feb. 2, 2023
Abstract
Isocyanides
(isonitriles
or
carbylamine)
have
been
intensively
used
in
organic
synthesis
to
prepare
a
diverse
variety
of
N‐heterocycles
on
the
basis
carbene‐like
reactivity
their
divalent
carbon
atom.
participate
reactions
involving
one,
two,
more
isocyanides.
Compared
popularity
single
isocyanide
reactions,
few
examples
two
isocyanides
reported.
In
this
review,
we
categorized
and
classified
literatures
especially
double
insertions
under
metal‐catalyzed
metal‐free
conditions
from
2014
2022.
magnified
image
Chinese Journal of Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 7, 2025
Comprehensive
Summary
Herein,
we
have
developed
a
facile
method
for
the
synthesis
of
various
polysubstituted
pyridine
derivatives
through
selective
6π‐electrocyclization
N
‐vinyl‐
α
,
β
‐unsaturated
nitrones.
It
was
found
that
gold
catalysts
promoted
carbon‐6π‐electrocyclization
nitrones
to
afford
6‐alkenyl
‐oxides
in
43%—75%
yields,
whereas
copper
facilitated
oxygen‐6π‐electrocyclization
give
6‐epoxy
pyridines
41%—83%
yields.
The
present
features
broad
substrate
scope,
good
functional
group
tolerance,
high
cyclization
selectivity,
and
diversity
scaffolds.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(29), P. 6028 - 6033
Published: Jan. 1, 2023
The
base
promoted
tandem
annulation
reaction
of
activated
cyclic
1,3-dipolarophiles
such
as
2-arylidene-1,3-indanediones,
2-(o-hydroxybenzylidene)-1,3-indanediones
and
3-methyleneoxindoles
with
functionalized
furo[2,3-d]pyrimidine-2,4-diones
was
systematically
investigated.
This
provided
efficient
synthetic
protocols
for
complex
dispiro/dispiro
fused
tricyclic
compounds
including
dispiro[indene-2,3'-cyclopentane-1',5''-pyrimidines],
dispiro[indoline-3,3'-cyclopentane-1',5''-pyrimidines]
spiro[cyclopenta[c]indeno[1,2-b]chromene-3,5'-pyrimidines]
in
good
yields
high
diastereoselectivity.
believed
to
proceed
via
sequential
ring-opening
the
furyl
ring,
formal
[3
+
2]
cycloaddition
o-hydroxyphenyl
group.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(23), P. 5043 - 5048
Published: June 6, 2024
Herein,
we
present
a
new
and
general
protocol
for
the
assembly
of
2,2′-bipyridyls
from
nonpyridine
substrates
without
using
any
metal
catalysts
or
organometallic
reagents.
The
process
starts
coupling
two
1,3-dienyl
isocyanides
followed
by
6π-electrocyclization/aromatization
cascade
featuring
simultaneous
formation
pyridine
rings
in
single
operation.
Notably,
this
strategy
is
also
applicable
to
construction
nonsymmetrical
2-(2-pyridyl)-quinolines/-quinoxalines.
Furthermore,
aggregation-induced
emission
(AIE)
characteristics
endow
our
approach
with
great
potential
biorelevant
fields.
Chemical Society Reviews,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
This
review
outlines
in
detail
strategies
for
state-of-the-art
synthetic
routes
and
demonstrates
various
interactions
from
the
synergistic
combination
of
C–H
functionalization
with
multiple
isocyanides
to
establish
complicated
reactions.
