The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 18, 2024
A
facile,
cost-effective,
and
sustainable
synthesis
of
substituted
triazines
from
primary
alcohols
by
newly
synthesized
nickel
pincer-type
complexes
(1–3)
has
been
described.
Herein,
we
report
the
a
set
three
well-defined
Ni(II)
O^N^O
complexes,
structurally
characterized
analytical,
spectral,
X-ray
diffraction
techniques.
Further,
are
explored
as
efficient
catalysts
(4
mol
%)
for
construction
2,4,6-substituted
1,3,5-triazines
readily
available
via
an
acceptorless
dehydrogenative
coupling
(ADC)
strategy.
wide
range
triazine
derivatives
(33
examples)
benzamidine/guanidine
hydrochloride
with
maximum
isolated
yield
92%
under
mild
conditions,
eco-friendly
H2O
H2
gas
only
byproducts.
plausible
mechanism
proposed
based
on
sequence
control
experiments.
Interestingly,
short
antiulcer
drug
irsogladine
large-scale
2,4-diphenyl-6-(p-tolyl)-1,3,5-triazine
highlight
convenience
current
methodology.
Green Synthesis and Catalysis,
Год журнала:
2023,
Номер
unknown
Опубликована: Окт. 1, 2023
The
synthesis
of
4-halo-functionalized
pyrazoles
by
electrochemical
cascade
reactions
between
N,N-dimethyl
enaminones
and
proper
hydrazine
reagents
in
the
presence
a
halogen
source
is
realized
at
room
temperature.
work
provides
tunable
efficient
accesses
to
4-chloro-
4-bromopyrazoles
aqueous
THF
(tetrahydrofuran)
without
using
any
transition
metal
reagent.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
streamlined
strategy
for
the
one-pot
synthesis
of
isoxazolone
analogues
has
been
developed
through
an
acceptorless
dehydrogenative
annulation
(ADA)
pathway
by
employing
new
Ru(II)
hydride
complexes
as
effective
catalysts.
New
(C1–C3)
tailored
with
N̂O
chelating
carbazolone
benzhydrazone
ligands
were
synthesized
and
their
formation
was
confirmed
using
analytical
spectral
techniques
including
FT-IR
NMR.
The
structural
configuration
featuring
octahedral
geometry
around
ion
precisely
determined
single-crystal
X-ray
diffraction
analysis.
Further,
catalytic
efficacy
titled
established
facile
productive
derivatives
from
a
diverse
range
benzyl
alcohols,
methyl
acetoacetate/ethyl
benzoylacetate
hydroxylamine
hydrochloride,
generating
excellent
yields
up
to
93%
under
well-suited
mild
conditions
1
mol
%
catalyst
loading.
sequence
time-dependent
control
experiments
unveiled
ADA
route,
indicating
initial
generation
4-methoxy
benzaldehyde
intermediate
followed
3-phenylisoxazol-5(4H)-one,
accompanied
release
water
hydrogen
byproducts.
Gram-scale
compound
indicates
industrial
relevance
our
synthetic
strategy.
short
medicinally
active
androgen
antagonist
illustrates
utility
present
protocol.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2494 - 2504
Опубликована: Фев. 7, 2024
We
report
the
atom-economic
and
sustainable
synthesis
of
biologically
important
3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxide
(DHBD)
derivatives
from
readily
available
aromatic
primary
alcohols
2-aminobenzenesulfonamide
catalyzed
by
nickel(II)-N∧N∧S
pincer-type
complexes.
The
synthesized
nickel
complexes
have
been
well-studied
elemental
spectroscopic
(FT-IR,
NMR,
HRMS)
analyses.
solid-state
molecular
structure
complex
2
has
authenticated
a
single-crystal
X-ray
diffraction
study.
Furthermore,
series
(24
examples)
utilizing
3
mol
%
Ni(II)
catalyst
through
acceptorless
dehydrogenative
coupling
benzyl
with
benzenesulfonamide.
Gratifyingly,
catalytic
protocol
is
highly
selective
yield
up
to
93%
produces
eco-friendly
water/hydrogen
gas
as
byproducts.
control
experiments
plausible
mechanistic
investigations
indicate
that
in
situ
generated
aldehyde
benzenesulfonamide
leads
desired
product.
In
addition,
large-scale
one
thiadiazine
unveils
synthetic
usefulness
current
methodology.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(24), С. 16967 - 16977
Опубликована: Ноя. 29, 2023
We
demonstrate
an
efficient
and
sustainable
strategy
for
the
direct
synthesis
of
2,4-disubstituted
quinazolines
by
arene
Ru(II)benzhydrazone
complex
via
eco-friendly
sequential
acceptorless
dehydrogenative
coupling
2-aminobenzhydrol
derivatives
benzyl
alcohols
first
time.
The
new
ruthenium(II)
general
formula
[(η6-p-cymene)Ru(L1)Cl]
(L1-acenaphthenequinone
hydrazone)
has
been
synthesized
characterized
analytical,
spectroscopic,
single-crystal
X-ray
diffraction
techniques.
A
broad
spectrum
have
successfully
derived
(25
examples)
from
with
various
using
1
mol
%
catalyst
loading
in
presence
NH4OAc.
present
protocol
is
highly
selective
produces
a
maximum
yield
95%
under
mild
reaction
conditions.
different
intermediates
detected
through
control
experiments
such
as
aldehyde,
2-aminobenzophenone,
benzylidene(amino)phenylmethanone,
1,2-dihydroquinazoline
are
isolated
authenticated
NMR
study.
Gratifyingly,
simple
atom
economic
release
water
hydrogen
gas
only
byproducts.
gram-scale
2-(4-methoxyphenyl)-4-phenylquinazoline
illustrates
synthetic
utility
protocol.
Current Organic Chemistry,
Год журнала:
2024,
Номер
28(4), С. 305 - 318
Опубликована: Фев. 1, 2024
Abstract::
This
study
aims
to
develop
a
practical
and
facile
one-pot
synthesis
of
2-
substituted
quinazolines.
Using
commercially
available
structurally
simple
ruthenium(
II)
complex
as
the
catalyst
synthesize
series
quinazoline
derivatives
via
acceptorless
dehydrogenative
coupling.
The
mechanism
this
reaction
was
explored
by
control
DFT
calculation.
protocol
offers
access
diverse
array
(52
examples)
in
moderate
excellent
yields
(29%-98%).
In
summary,
we
have
developed
an
efficient
ruthenium
(II)-catalyzed
ADC
under
air
atmosphere.
only
produces
hydrogen
water
by-products,
serving
sustainable
atom-efficient
synthetic
approach.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(16), С. 11148 - 11160
Опубликована: Авг. 1, 2024
We
report
an
efficient
and
sustainable
synthesis
of
highly
substituted
pyrimidines
promoted
by
nickel(II)-NNS
pincer-type
complexes
via
acceptorless
dehydrogenative
annulations
readily
available
alcohols,
malononitrile,
guanidine/benzamidine
salt
under
eco-friendly
conditions
for
the
first
time.
Different
sets
Ni(II)
(
