Abstract
A
formal
[4+3]
cycloaddition
of
2‐alkylidenetrimethylene
carbonates
with
quinazoline‐derived
azomethine
imines
is
described.
Under
Pd
catalysis,
the
reaction
works
efficiently
under
room
temperature
to
afford
angular
quinazoline‐fused
seven‐membered
N,N,O
‐heterocycles.
variety
cyclic
and
were
well
tolerated
mild
conditions.
This
work
demonstrates
synthetic
utility
decarboxylative
cycloadditions
for
synthesis
polycyclic
aromatic
molecules.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8363 - 8375
Опубликована: Июнь 7, 2024
Palladium-catalyzed
decarboxylation
of
5-methylene-1,3-oxazinan-2-ones
and
5-methylene-1,3-dioxan-2-ones
to
generate
aza-π-allylpalladium
oxa-π-allylpalladium
1,4-dipoles
for
[4
+
2]
cycloaddition
reaction
with
1,3,5-triazinanes
was
developed,
affording
a
wide
range
hexahydropyrimidine
1,3-oxazinane
derivatives
in
good
excellent
yields
(up
99%).
The
acyclic
sulfonamido-substituted
allylic
carbonates
as
1,4-dipole
precursors
also
apply
the
developed
synthesized
strategy,
achieving
synthesis
hexahydropyrimidines.
Moreover,
situ-generated
undergoing
dimeric
4]
were
demonstrated
by
construction
1,5-diazocane
derivatives.
Abstract
Catalytic
dearomative
cycloaddition
involving
the
C2–C3
bond
of
indoles
is
a
powerful
strategy
for
synthesis
fused
indoline
scaffolds.
Through
cycloaddition/annulation,
planar
indole
substrates
can
be
readily
transformed
into
rigid,
three-dimensional
polycyclic
complex
structures
in
one
step.
Molecules
with
architectural
complexity
are
generally
considered
to
have
drug-like
properties.
Hence,
annulation
products
tremendous
potential
discovering
therapeutic
properties,
and
this
has
become
an
important
part
medicinal
chemistry
toolbox.
Using
appropriate
catalyst
control,
desirable
stereoselectivity
achieved.
Previous
literature
reports
reveal
that
[3+2]-cycloadditions
been
extensively
studied.
In
contrast,
catalytic
[4+2]-cycloaddition/dearomatization
much
less
investigated.
short
review,
we
focus
specifically
on
six-membered
ring
annulations
via
[4+2]-cycloaddition
discuss
various
methods
developed
toward
objective.
1
Introduction
2
[4+2]-Cycloaddition/Annulation
Indoles
2.1
Electron-Rich
2.1.1
Transition-Metal
Catalysis
2.1.2
Organocatalysis
2.2
Electron-Deficient
2.2.1
2.2.2
3
Summary
Outlook
Abstract
A
formal
[4+3]
cycloaddition
of
2‐alkylidenetrimethylene
carbonates
with
quinazoline‐derived
azomethine
imines
is
described.
Under
Pd
catalysis,
the
reaction
works
efficiently
under
room
temperature
to
afford
angular
quinazoline‐fused
seven‐membered
N,N,O
‐heterocycles.
variety
cyclic
and
were
well
tolerated
mild
conditions.
This
work
demonstrates
synthetic
utility
decarboxylative
cycloadditions
for
synthesis
polycyclic
aromatic
molecules.
