Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(19), P. 3375 - 3379
Published: May 8, 2023
An
efficient
rhodium-catalyzed
synthesis
of
dihydro-3,1-benzoxazine
derivatives
has
been
accomplished
from
aniline-derived
1,3-amino
alcohols
and
N-sulfonyl-1,2,3-triazole.
The
developed
reaction
demonstrates
the
new
reactivity
azavinyl
carbenes
allows
access
to
diverse
substituted
dihydro-3,1-benzoxazines
in
good
yields.
Importantly,
was
readily
extended
diols
could
be
used
for
selective
protection
amino
with
N-sulfonyl-1,2,3-triazole
as
protecting
reagent.
Chemical Reviews,
Journal Year:
2022,
Volume and Issue:
122(15), P. 13108 - 13205
Published: July 19, 2022
Readily
accessible
and
shelf-stable
1,2,3-triazole
its
analogues
such
as
pyridotriazole,
triazoloindole,
benzotriazole,
thiadiazole
exist
in
equilibrium
with
their
ring-opened
isomers,
viz.,
diazo
compounds.
These
isomers
could
be
trapped
by
various
metal
catalysts
(e.g.,
Rh,
Pd,
Cu,
Co,
Ag,
etc.)
to
generate
the
corresponding
carbenoids
extrusion
of
nitrogen.
As
a
consequence,
these
unique
N-heterocycles
facilitate
access
realm
N-containing
complex
structural
motifs
biological
importance
through
denitrogenative
transformations
transannulations,
insertions,
ylide
formation,
rearrangements
trapping
diverse
range
coupling
partners
alkenes,
alkynes,
nitriles,
carbo/heterocycles,
X-H/C-X
bonds,
etc.).
Hence,
suitably
substituted
triazole
derivatives
have
emerged
efficient
surrogates
compounds
for
generation
reactive
during
past
decades.
In
this
comprehensive
review,
we
aim
discuss
detail
remarkable
advancement
synthesis
synthetic
applications.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 5, 2025
A
base-promoted
regioselective
formal
[3
+
2]
annulation
of
pyridinium
ylides
with
bromoalkynes
is
reported,
producing
a
series
substituent-diverse
indolizines
in
generally
good
yields.
mild
K2CO3-promoted
three-component
cyclization
and
at
2:1
molar
ratio
delivered
C2-acylmethylated
indolizines,
whereas
C2-brominated
were
generated
starting
from
bearing
strong
electron-withdrawing
groups
the
unit
by
using
2,2,6,6-tetramethyl-1-piperidinyloxy
as
dehydrogenating
reagent.
The
current
synthetic
methodology
offers
controllable
modular
approach
to
access
different
substitution
patterns,
featuring
wide
substrate
scope,
functional
group
compatibility,
complete
regioselectivity
without
demand
any
transition-metal
catalysts.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(3), P. 1836 - 1845
Published: Jan. 16, 2024
A
regioselective
visible-light-mediated
denitrogenative
alkene
insertion
of
1,2,3-benzotriazin-4(3H)-ones
was
developed
to
access
3-substituted
isoindolinones,
an
important
structural
motif
present
in
many
biologically
active
molecules
and
natural
products.
Notably,
divergent
reactivity
achieved
by
switching
from
reported
nickel
catalysis
(where
C3-substituted
3,4-dihydroisoquinolin-1(2H)-ones
form)
photocatalysis,
where
photocatalytic
denitrogenation
a
subsequent
nitrogen-mediated
hydrogen
atom
shift
lead
exclusive
isoindolinone
formation.
The
reaction
is
compatible
with
activated
terminal
alkenes
cyclic
α,β-unsaturated
esters
ketones,
wide
functional
group
tolerance
for
N-substitution
the
1,2,3-benzotriazin-4(3H)-ones.
utility
this
procedure
highlighted
gram-scale
synthesis
postsynthetic
amidation.
To
understand
origin
unique
product
selectivity,
experimental
computational
mechanistic
studies
were
performed.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(21), P. 8500 - 8504
Published: Oct. 12, 2020
An
efficient
radical
transannulation
reaction
of
pyridotriazoles
with
isothiocyanates
and
xanthate
esters
was
developed.
This
method
features
conversion
into
two
N-fused
heterocyclic
aromatic
systems—imino-thiazolopyridines
oxo-thiazolopyridine
derivatives—via
one-step
Co(II)-catalyzed
proceeding
via
a
mechanism.
The
synthetic
usefulness
the
developed
illustrated
in
synthesis
amino
acid
derivatives
further
transformations
obtained
products.
Journal of Agricultural and Food Chemistry,
Journal Year:
2021,
Volume and Issue:
69(23), P. 6475 - 6484
Published: June 2, 2021
To
improve
the
effect
of
pine
rosin
in
plant
fungicides,
four
series
dehydroabietyl-1,3,4-thiadiazole
derivatives
from
natural
product
were
synthesized.
Based
on
evaluation
vitro
antifungal
activity
against
Sclerotinia
sclerotiorum,
Botrytis
cinerea,
Fusarium
oxysporum,
and
Magnaporthe
oryzae,
rosin-based
1,3,4-thiadiazole
compounds
containing
thiophene
heterocycles
screened.
Notably,
compound
3e
[dehydroabietyl-(1,3,4-thiadiazol-2-yl)-5-nitrothiophene-2-carboxamide]
exhibited
excellent
property
F.
oxysporum
with
an
EC50
0.618
mg/L,
which
was
lower
than
that
positive
control
carbendazim
(0.649
mg/L).
The
vivo
results
showed
exerted
a
protective
cucumber
plants.
Physiological
biochemical
studies
primary
mechanism
action
it
changed
mycelial
morphology,
increased
cell
membrane
permeability,
inhibited
synthesis
ergosterol
mycelia.
Furthermore,
quantitative
structure–activity
relationship
revealed
frontier
orbital
energy
molecule
had
key
role
through
conjugation
electrostatic
interaction
between
receptors
target.
Thus,
present
study
highlighted
application
fungicidal
candidates
exploited
efficient
pesticides
for
sustainable
crop
production.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(20), P. 2796 - 2799
Published: Jan. 1, 2024
We
report
light-induced
arylation
(alkylation)
for
the
synthesis
of
diarylmethanes,
bis(diarylmethyl)benzenes,
arylalkylmethanes,
and
triarylmethanes
from
readily
accessible
N
-sulfonylhydrazones
aryl/alkylboronic
acids
with
aid
Cs
2
CO
3
.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(3), P. 1753 - 1761
Published: Jan. 22, 2024
A
novel
and
flexible
domino
reaction
of
aurones
with
pyridin-2-yl
active
methylene
compounds
promoted
by
I2/BF3
has
been
developed
to
afford
spirodihydroindolizines
indolizines
in
a
controllable
manner.
When
the
was
performed
1,2-dichloroethane
at
80
°C,
variety
were
obtained,
whereas
it
almost
exclusively
provided
series
when
mixed
solvent
N,N-dimethylformamide
relatively
higher
temperature
100
°C.
Being
metal-free,
excellent
product
selectivity,
high
atom
economy,
good
functional
group
tolerance,
feasibility
for
large-scale
synthesis
are
salient
features
methodology.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(23), P. 9303 - 9307
Published: Nov. 24, 2020
The
unprecedented
dearomative
migratory
rearrangement
reactions
of
2-oxypyridines
with
N-sulfonyl-1,2,3-triazoles
have
been
developed
under
rhodium
catalysis,
providing
a
reliable
and
efficient
protocol
for
accessing
N-substituted
2-pyridones.
These
two
distinct
rearrangements
feature
the
controllable
1,4-migration
carbonate
group
from
O-to-C
as
well
O-to-N
1,6-migration
an
acyl
via
α-imino
carbene
transfer.
Moreover,
reaction
pyridotriazoles
delivers
products
in
high
efficiency.
