Abstract
A
microwave‐assisted
synthesis
of
7‐amino‐1,2,4‐triazolo[1,5‐
a
][1,3,5]triazine‐2‐propanamides
was
developed
using
three‐component,
catalyst‐free
reaction
cyanamide
and
trimethyl
orthoformate
with
3‐(5‐amino‐1
H
‐1,2,4‐triazol‐3‐yl)propanamides
(
3
).
The
tolerated
structurally
diverse
substrates
proceeded
chemo‐
regio‐selectively,
affording
the
target
compounds
in
high
purity
5–10
minutes.
convenient
chromatography‐free
isolation
purification
products
add
practicality
to
this
method.
structural
features
prepared
were
investigated
dynamic
NMR
spectroscopy,
X‐ray
crystallography
computational
chemistry
calculations.
performed
on
representative
compound,
3‐(7‐amino‐1,2,4‐triazolo[1,5‐
][1,3,5]triazin‐2‐yl)‐
N
‐(4‐benzyl)propanamide
4
l
),
showed
overall
molecular
conformation
adopt
shape
letter
C.
Notable
localisation
π‐electron
density
is
found
within
1,2,4‐triazolo[1,5‐
][1,3,5]triazine
system;
relatively
short
C−NH
2
bond
consistent
restricted
rotation
about
bond.
This
study
also
presents
detailed
analysis
interactions
DFT
QTAIM
methods
focus
hydrogen‐bonding
π‐stacking
that
influence
packing
.
findings
reveal
significant
roles
N−H⋅O,
N−H⋅N
C−H⋅N
interactions,
along
electrostatically
enhanced
π⋅π
contacts.
broad
screening
for
insecticidal,
fungicidal
herbicidal
properties
identified
several
potent
activity
against
Matricaria
inodora
Journal of Materials Chemistry A,
Год журнала:
2023,
Номер
11(26), С. 13876 - 13888
Опубликована: Янв. 1, 2023
Hydrogen
transfer
from
nitroamino
to
nitroimino
promotes
density,
energy
and
safety
of
energetic
materials
suggesting
excellent
application
prospects
in
designing
next
generation
high
density
materials.
Crystal Growth & Design,
Год журнала:
2022,
Номер
23(1), С. 207 - 215
Опубликована: Дек. 21, 2022
1,2,4-Triazol-3-one
(TO)
is
an
important
nitrogen-rich
heterocycle
in
synthesis
chemistry.
In
the
field
of
energetic
materials,
some
strategies
are
applied
to
prepare
TO-derived
materials.
However,
none
them
can
be
used
as
a
heat-resistant
material
due
their
lower
decomposition
temperatures.
this
paper,
series
TO
derivatives
4–13
were
prepared
from
5-oxo-4,5-dihydro-1H-1,2,4-triazole-3-carboxylic
acid.
These
compounds
fully
characterized
by
using
elemental
analysis,
1H
and
13C
NMR
spectroscopy,
IR
MS.
The
crystal
structures
fused-ring
compound
6
perchlorate
8
further
identified
single-crystal
X-ray
diffraction.
Most
exhibit
good
thermostability
(Td
=
166.5–324.5
°C),
low
sensitivities
(impact
sensitivity
IS
≥
20
J;
friction
FS
360
N),
detonation
performance
(Dv
7905–8753
m
s–1),
positive
heats
formation
(ΔHf
295.9–1121.1
kJ
mol–1),
except
9
92
°C;
15
240
N).
Among
these
target
molecules,
with
high
temperature
324.5
density
(ρ
1.859
g
cm–3),
(IS
>
40
decent
8406
s–1;
P
29.2
GPa)
superior
traditional
explosive
hexanitrostilbene
318
ρ
1.750
cm–3;
5
N;
Dv
7612
26.3
insensitive
thermostable
material.
Molecules,
Год журнала:
2025,
Номер
30(3), С. 506 - 506
Опубликована: Янв. 23, 2025
The
thermal
characterisation
and
toxicity
profile
of
a
class
disubstituted
heterofused
triazinones
were
revealed
in
this
article
for
the
first
time.
behaviour
molecules
1–12
was
investigated
by
means
TG
DSC
analyses
performed
an
air
atmosphere
coupled
TG/FTIR
technique
nitrogen
atmosphere.
heating
affects
both
stability
compounds
degradation
mechanism.
A
two-step
occurs
air,
while
one-step
takes
place
nitrogen,
preceded
melting
process.
Compound
3
shows
highest
stability,
molecule
10—the
lowest.
decomposition
studied
heterocyclic
begins
with
bicyclic
system,
resulting
formation
volatile
gaseous
products
such
as
ammonia/hydrazine,
hydrogen
cyanide,
carbon
dioxide,
isocyanates.
In
further
stage,
mainly
aromatic
are
released,
their
chemical
composition
depends
on
presence
type
substituents
at
phenyl
benzyl
moieties.
addition,
profiles
assessed
animal
(zebrafish)
cellular
(erythrocytes)
models,
antihaemolytic
activity
evaluated
AAPH-
H2O2-induced
haemolysis
inhibition
assays.
It
found
that
all
tested
safe
developing
zebrafish
red
blood
cells,
they
able
to
effectively
protect
erythrocytes
from
oxidative
damage.
These
favourable
properties
make
them
promising
drug
candidates
suitable
vivo
studies.
Dalton Transactions,
Год журнала:
2024,
Номер
53(13), С. 6100 - 6111
Опубликована: Янв. 1, 2024
Novel
energetic
cyano
derivatives
of
polynitro
hexaazaisowurtzitanes
surpass
the
benchmark
CL-20
in
energy
content,
as
well
frictional
and
thermal
stability.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(10), С. 6783 - 6792
Опубликована: Апрель 25, 2024
Tetrazoles
and
their
derivatives
are
essential
for
compound
synthesis
due
to
versatility,
effectiveness,
stability
in
air,
cost-efficiency.
This
has
stimulated
interest
developing
techniques
production.
In
this
work,
four
compounds,
tetrazolo[1,5-
Chemical Communications,
Год журнала:
2024,
Номер
60(76), С. 10588 - 10591
Опубликована: Янв. 1, 2024
In
this
paper,
three
neutral
heterocycle-triazolotriazine
compounds
featuring
multiple
amino
groups
and
nitro
were
designed
synthesized.
Among
them,
2
6
exhibit
high
detonation
performance
(
