The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(19), P. 14131 - 14139
Published: Sept. 18, 2023
An
efficient
methodology
to
form
4-alkoxy-
and
4-aryloxybenzo[d][1,2,3]triazines
via
an
intramolecular
heterocyclization
of
1-azido-2-[isocyano(p-tosyl)methyl]benzenes
under
basic
conditions
has
been
developed.
DFT
calculations
have
performed
further
understand
the
mechanism
this
heterocyclization,
which
occurs
in
good
excellent
yields
with
a
broad
scope.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(18), P. 12891 - 12901
Published: Aug. 24, 2023
An
air-tolerant
mechanoredox/nickel
cocatalyzed
cross
electrophile
coupling
of
benzotriazinones
with
alkyl
(pseudo)halides
is
developed
by
liquid-assisting
grinding
in
the
presence
manganese
powders
and
strontium
titanate
as
a
reductant
cocatalyst,
respectively.
Mechanical
activation
metal
surfaces
via
ball
milling
eliminates
chemical
activator
for
manganese,
while
mechanoredox
cocatalysis
remarkably
improves
aryl/alkyl
piezoelectricity-mediated
radical
generation
from
halides.
Both
display
reactivities
different
those
conventional
thermal
chemistry
solution.
The
scope
reaction
demonstrated
26
examples,
showing
high
chemoselectivity
bromides
vs
chlorides.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(12), P. 2371 - 2375
Published: March 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.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(11), P. 2623 - 2628
Published: April 20, 2024
Abstract
A
palladium
catalyst
system
based
on
PdCl
2
(PPh
3
)
or
(dppf)
is
reported
for
Suzuki‐type
coupling
of
both
N
‐aryl
and
alkyl
benzotriazinones
with
aryl/alkenyl
boronic
acids
to
afford
a
series
ortho
‐aryl/alkenyl
benzamides
in
yields
up
99%,
showing
improvements
catalytic
efficiency,
substrate
scope
practicality.
Scope
limitations
the
improved
protocol
have
been
demonstrated
more
than
40
examples,
including
multigram‐scale
synthesis
activated
o
‐biphenyl
amide.
Large
electronic
steric
effects
from
acid
counterpart
observed,
implying
transmetallation
boron
should
be
involved
rate‐determining
step
cycle.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(49), P. 9012 - 9016
Published: Dec. 5, 2022
An
expedient
synthesis
of
benzo[c][1,2]dithiol-3-ones
via
metal-free
denitrogenative
transannulation
benzotriazinones
is
developed,
which
represents
the
first
example
acid-mediated
heteroannulation
benzotriazinones.
This
newly
discovered
reactivity
enables
streamline
diverse
in
decent
yields
by
using
sodium
sulfide
as
sulfur
source
under
simple
reaction
conditions.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(29), P. 5443 - 5447
Published: July 13, 2023
We
herein
developed
a
palladium-catalyzed
reaction
of
[1,2,3]-benzotriazin-4(3H)-ones
with
DABAL-Me3
[bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane
adduct],
cheap,
stable,
and
solid
organoaluminum
reagent.
In
the
presence
Pd(OAc)2/XantPhos
as
commercially
available
catalyst,
underwent
denitrogenative
coupling
to
afford
wide
array
N-aryl
amides
derived
from
ortho-methylated
carboxylic
acids.
Under
same
catalytic
conditions,
ortho-ethylation
could
also
be
achieved
by
using
triethylaluminum.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(21), P. 6184 - 6193
Published: Jan. 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.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 21, 2025
An
efficient
metal-free
approach
for
synthesizing
N-aryl-
and
N-alkyl
phthalimide
derivatives
from
1,2,3-benzotriazin-4(3H)-ones
is
described.
The
reaction
likely
proceeds
via
a
denitrogenative
cyanation
pathway,
utilizing
TMSCN
as
the
cyanide
source.
This
method
straightforward
well
scalable
supports
wide
range
of
substrates
with
high
functional
group
tolerance,
yielding
diverse
in
good
to
excellent
yields.
utility
this
further
highlighted
by
successful
synthesis
tyrosinase
inhibitor
analogue
yield.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 21, 2025
An
unexpected
electrochemical
cascade
reaction
of
1,2,3-benzotriazinones
with
alkynes
to
assemble
3,4-dihydroisoquinolin-1(2H)-ones
has
been
developed,
which
avoids
the
use
pressurized
H2,
any
metal
catalysts,
and
stoichiometric
redox
agents.
This
route
tolerates
a
wide
range
functional
groups
in
both
reactants
can
be
performed
under
an
air
atmosphere.
The
process
continuous
cathodic
reduction
was
demonstrated
by
control
experiments
cyclic
voltammograms.
Moreover,
gram-scale
confirmed
potential
this
environmentally
benign
method
for
practical
applications.
