FirePhysChem,
Год журнала:
2022,
Номер
3(1), С. 78 - 87
Опубликована: Сен. 20, 2022
In
recent
years,
the
development
of
novel
advanced
energetic
materials
has
significantly
shifted
toward
nitrogen
heterocyclic
derivatives,
which
demonstrate
a
great
potential
for
multipurpose
application
patterns.
Among
known
heterocycles
tetrazine
ring
is
well-known
structural
scaffold
used
in
preparation
various
high-energy
materials.
The
majority
energy-rich
substances
incorporating
subunit
exhibit
high
thermal
stability,
good
detonation
performance
and
low
sensitivity
to
mechanical
stimuli
defines
their
practical
usability.
this
review,
main
achievements
on
synthesis
tetrazine-based
reported
last
decade
are
summarized.
Potential
applications
presented
compounds
especially
emphasized.
Journal of Medicinal Chemistry,
Год журнала:
2021,
Номер
64(4), С. 1786 - 1815
Опубликована: Фев. 11, 2021
Incorporation
of
heterocycles
into
drug
molecules
can
enhance
physical
properties
and
biological
activity.
A
variety
heterocyclic
groups
is
available
to
medicinal
chemists,
many
which
have
been
reviewed
in
detail
elsewhere.
Oxadiazoles
are
a
class
heterocycle
containing
one
oxygen
two
nitrogen
atoms,
three
isomeric
forms.
While
the
1,2,4-
1,3,4-oxadiazoles
seen
widespread
application
chemistry,
1,2,5-oxadiazoles
(furazans)
less
common.
This
Review
provides
summary
furazan-containing
chemistry
development
programs
from
analysis
both
patent
academic
literature.
Emphasis
placed
on
that
reached
clinical
or
preclinical
stages
development.
The
examples
provided
herein
describe
pharmacology
activity
furazan
derivatives
with
comparative
data
where
possible
for
other
pharmacophores
commonly
used
chemistry.
Physical Chemistry Chemical Physics,
Год журнала:
2023,
Номер
25(25), С. 16763 - 16771
Опубликована: Янв. 1, 2023
Excited-state
aromaticity
(ESA)
and
antiaromaticity
(ESAA)
are
by
now
well-established
concepts
for
explaining
photophysical
properties
photochemical
reactivities
of
cyclic,
conjugated
molecules.
However,
their
application
is
less
straightforward
than
the
corresponding
process
which
thermal
chemistry
such
systems
rationalized
in
terms
ground-state
(GSA)
(GSAA).
Recognizing
that
harmonic
oscillator
model
(HOMA)
provides
an
easy
way
to
measure
on
geometric
grounds,
it
therefore
notable
this
yet
be
parameterized
excited
states.
Against
background,
we
here
present
a
new
parameterization
HOMA
-
termed
HOMER
T1
state
both
carbocyclic
heterocyclic
compounds
based
high-level
quantum-chemical
calculations.
Considering
CC,
CN,
NN
CO
bonds
testing
parametrization
using
calculated
magnetic
data
as
reference,
find
description
ESA
ESAA
superior
afforded
original
scheme,
reaches
same
overall
quality
does
GSA
GSAA.
Furthermore,
demonstrate
derived
parameters
can
used
predictive
modeling
at
very
different
levels
theory.
Altogether,
results
highlight
potential
facilitate
future
studies
ESAA.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(1), С. 174 - 182
Опубликована: Дек. 11, 2023
A
majority
of
known
and
newly
synthesized
energetic
materials
comprise
polynitrogen
or
nitrogen–oxygen
heterocycles
with
various
explosophores.
However,
available
structural
combinations
these
organic
scaffolds
are
finite
about
to
reach
their
limits.
Herein,
we
present
the
design
synthesis
a
series
sulfur-containing
polyazole
structures
comprising
1,3,4-thiadiazole
furazan
rings
linked
by
C–C
bonds
enriched
nitro
azo
functionalities.
In
terms
detonation
performance,
all
1,3,4-thiadiazole-furazan
assemblies
(D
=
7.7–7.9
km
s–1;
P
26–28
GPa)
lie
between
powerful
explosive
TATB
8.0
31
melt-cast
material
TNT
6.9
23
GPa).
series,
azo-bridged
derivative
5
seems
be
most
practically
interesting,
as
it
combines
relatively
high
performance
7.9
28
GPa),
very
thermal
stability
(271
°C),
insensitivity
friction.
By
functional
properties,
outperforms
benchmark
heat-resistant
hexanitrostilbene
(HNS).
To
best
our
knowledge,
this
is
first
example
an
alliance
rare
case
high-energy
materials,
which
can
certainly
considered
evolutionary
step
in
science.
Dalton Transactions,
Год журнала:
2023,
Номер
52(22), С. 7673 - 7683
Опубликована: Янв. 1, 2023
The
preparation
of
multipurpose
high-energy
materials
for
space
technologies
remains
a
challenging
task
and
such
usually
require
special
precautions
fine
tunability
their
functional
properties.
To
unveil
new
opportunities
en
route
to
high-performance
energetic
materials,
novel
potential
melt-castable
explosives
plasticizers
incorporating
(1,2,3-triazolyl)furazan
scaffold
enriched
with
nitro
nitratomethyl
explosophoric
functionalities
were
synthesized.
successful
implementation
the
regiodivergent
approach
enabled
regioisomeric
(nitratomethyltriazolyl)furazans
that
possessed
significantly
different
physicochemical
properties
classifying
target
as
substances
or
plasticizers.
Hirshfeld
surface
calculations
supported
by
energy
framework
plots
also
performed
better
understand
relationship
between
molecular
structure
sensitivity.
All
prepared
(1,2,3-triazolyl)furazans
show
high
nitrogen-oxygen
contents
(76-77%),
good
experimental
densities
(up
1.72
g
cm-3)
positive
enthalpies
formation
(180-318
kJ
mol-1)
resulting
in
detonation
performances
(D
=
7.1-8.0
km
s-1;
P
21-29
GPa).
Overall,
this
work
unveils
strategies
construction
balanced
various
applications.
Russian Chemical Reviews,
Год журнала:
2024,
Номер
93(2), С. RCR5109 - RCR5109
Опубликована: Янв. 16, 2024
The
study
of
high-energy
materials
based
on
poly
nitrogen-
and
nitrogen-oxygen-containing
heterocycles
is
one
the
most
important
relevant
modern
interdisciplinary
research
areas
at
intersection
organic
physical
chemistry
science.
Among
such
heterocycles,
1,2,4-oxadiazole
ring
a
rather
interesting
building
block
for
synthesis
new
energetic
compounds.
Although
1,2,4-oxadiazoles
has
been
developed
more
than
100
years,
these
have
only
recently
become
known
are
currently
"hot
spots"
in
this
field
This
review
systematizes
published
methods
features
reactivity
1,2,4-oxadiazole-based
Mono-
bis(1,2,4-oxadiazoles)
as
well
structures
containing
other
azoles
pyrazole,
1,2,5-oxadiazole,
1,3,4-oxadiazole,
1,2,3-triazole,
1,2,4-triazole
tetrazole
considered.
For
series
structurally
similar
compounds,
their
physicochemical
properties
summarized
factors
affecting
particular
parameter
discussed.<br>
Bibliography
—
123
references.
Abstract
The
nitrogen
containing
1,2,3‐benzotriazin‐4(3
H
)‐one
is
structurally
worthwhile
system
for
its
notable
applications
in
the
synthesis
of
N─
,
O
─
and
S─
heterocycles
bears
pivotal
significant
usage
pharmaceutical
industrial
chemicals.
Today
most
common
items
like
dyes,
cosmetics,
sanitizers,
insecticides
plastics
are
based
on
heterocyclic
moieties.
Different
starting
materials
used
industrially
formation
diverse
but
a
valuable
structure
to
prepare
numerous
products.
These
conversions
radiation
or
metal‐catalyzed
denitrogenation
annulation
type
reactions
provide
easy,
one‐step
atom‐economical
route.
vast
significance
their
cheap
make
this
subject
interesting
scientific
researchers
industrialists.
This
mini
review
summarizes
recent
developments
transformation
ring
various
other
structures
phenanthridinones,
isoquinolones,
coumarin‐1‐imines,
benzamides,
pyrroloquinazolinones,
indolin‐1‐ones,
1,2‐benzisoselenazol‐3(2
)‐ones
benzofuranones.
Some
emerging
drugs
ebselen,
losartan,
irbesartan,
luotonin
A,
deoxyvasicinone
mackinazolinone
have
been
successfully
synthesized
from
differently
substituted
benzotriazinones.
