The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(21), С. 16043 - 16048
Опубликована: Окт. 15, 2024
The
dihydroisoquinolones
skeleton
is
ubiquitous
in
natural
products
and
biological
molecules.
Reported
strategies
for
constructing
usually
require
noble
metal
catalysts
or
stoichiometric
oxidants,
which
limit
their
wide
applications.
Herein,
we
developed
a
photoredox
catalyzed
tandem
denitrogenative
[4
+
2]
annulation
reaction
of
1,2,3-benzotriazin-4(3H)-ones
with
terminal
olefins.
A
variety
can
be
accessed
moderate
to
excellent
yield.
This
protocol
features
high
atom-economy,
mild
conditions,
external
oxidant-free,
enabling
the
synthesis
various
substituted
dihydroisoquinolones.
Organic Letters,
Год журнала:
2024,
Номер
26(12), С. 2371 - 2375
Опубликована: Март 11, 2024
We
report
a
new
protocol
for
the
synthesis
of
substituted
benzotriazin-4(3H)-ones
which
are
underrepresented
heterocyclic
scaffolds
with
important
pharmacological
properties.
Our
method
exploits
acyclic
aryl
triazine
precursors
that
undergo
photocyclization
reaction
upon
exposure
to
violet
light
(420
nm).
Continuous
flow
reactor
technology
is
exploited
afford
excellent
yields
in
only
10
min
residence
time
no
additives
or
photocatalysts
needed.
The
underlying
mechanism
appears
be
based
on
an
unprecedented
variation
classical
Norrish
type
II
concomitant
fragmentation
and
formation
N–N
bonds.
Scalability,
process
robustness,
green
credentials
this
intriguing
transformation
highlighted.
Chemical Communications,
Год журнала:
2024,
Номер
60(26), С. 3571 - 3574
Опубликована: Янв. 1, 2024
Herein,
a
novel
Pd-catalyzed
denitrogenation/vinylation
of
benzotriazinones
using
vinylene
carbonate
as
the
vinylation
reagent
is
reported.
This
transformation
demonstrates
an
unprecedented
skeletal
editing
approach,
effectively
converting
NN
to
CC
fragments
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(21), С. 6184 - 6193
Опубликована: Янв. 1, 2024
An
efficient
metal-free
approach
for
the
synthesis
of
isoindolinones
and
isoquinolinones
from
1,2,3-benzotriazin-4(3
H
)-ones
via
electron
donor–acceptor
(EDA)
complex
formation
under
visible
light
is
described.
Molecules,
Год журнала:
2025,
Номер
30(11), С. 2397 - 2397
Опубликована: Май 30, 2025
An
efficient
Ni-catalyzed,
Mn-mediated
denitrogenative
cross-electrophile
coupling
of
N-alkyl-1,2,3-benzotriazinones
with
alkyl
tosylates
and
mesylates
for
access
to
o-alkyl
secondary
benzamides
is
reported.
The
method
uses
inexpensive
non-anhydrous
dimethyl
acetamide
(DMA)
in
combination
tetrabutyl
ammonium
iodide
(TBAI)
as
a
co-catalyst
convert
sulfonates
into
iodides
situ.
Scope
limitations
the
protocol
have
been
demonstrated
by
>30
examples
yields
up
91%,
showing
large
electronic
effect
from
N-substituent
benzotriazinones.
unexpected
steric
acceleration
has
observed
core
benzotriazinones,
not
only
promising
highly
2-alkyl-2,3-disubstituted
but
also
shedding
light
on
rate-limiting
steps
catalytic
cycle.
Chemistry - An Asian Journal,
Год журнала:
2023,
Номер
18(21)
Опубликована: Сен. 15, 2023
A
palladium-catalyzed
denitrogenative
transannulation
strategy
to
access
various
3-substituted
isocoumarin-1-imine
frameworks
using
1,2,3-benzotriazin-4(3H)-ones
and
terminal
alkynes
is
described.
The
reaction
highly
regioselective
tolerates
a
wide
range
of
functional
groups.
believed
proceed
via
five-membered
palladacycle
intermediate
extruding
environmentally
benign
molecular
nitrogen
as
by-product.
utility
this
method
was
showcased
through
the
one-pot
synthesis
biologically
relevant
isocoumarin
scaffolds.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(36), С. 7295 - 7299
Опубликована: Янв. 1, 2023
An
eco-friendly
approach
for
electrochemical
radical
cascade
annulation
of
1,2,3-benzotriazinones
with
alkynes
is
described.
Under
catalyst-free
and
external
reductant-free
electrolysis
conditions,
a
range
isoquinolin-1(2H)-ones
were
obtained
in
moderate
to
good
yields.
Cyclic
voltammetry
control
studies
suggest
that
the
reaction
proceeds
via
pathway.
Furthermore,
this
could
be
easily
scaled
up.
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
13(7)
Опубликована: Май 17, 2024
Abstract
Denitrogenative
organic
transformations
and
related
reactions
are
a
class
of
significant
approaches
for
carrying
out
unusual
C−C/C‐heteroatom
(C−O,
C−N,
C−S)
bond‐forming
that
usually
promoted
by
Ru,
Ir,
Pd,
Ni,
Cu
metal
catalysts.
In
this
trait,
numerous
methods
were
adopted
to
synthesize
several
pharmaceutically
valuable
N
‐
O
‐containing
heteroaromatics
using
1,2,3‐benzotriazin‐4(3
H
)‐one
as
an
electrophilic
coupling
partner.
This
review
involves
the
recent
achievements
metal/organo‐catalyzed
thermal
visible‐light
mediated
denitrogenative
with
)‐ones
towards
synthesis
imperative
‐heteroaromatic
compounds.
addition,
oxidant‐free
ortho
‐functionalization
benzotriazinones
suitable
nucleophilic
partners
have
been
discussed.
particular,
most
novel
employing
Ni
Pd
catalysts
emerged
exhibited.
Specific
attention
has
paid
offering
detailed
mechanistic
pathway
explain
role
mechanism
in
absence
under
thermal/visible
light
medium.
