The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 5, 2025
An
efficient
one-step
protocol
has
been
developed
to
access
a
variety
of
2-amino-1,3-benzoxazine
derivatives
via
tetrabutylammonium
iodide-mediated
electrochemical
desulfurative
cyclization
isothiocyanates
and
2-aminobenzyl
alcohols.
The
reaction
proceeds
through
cycle
involving
in
situ
iodine
generation,
cyclization,
iodide
regeneration,
efficiently
forming
intermolecular
C–O
C–N
bonds
affording
2-amino-1,3-benzoxazines
moderate
excellent
yields.
practical
utility
this
strategy
is
evidenced
by
its
broad
substrate
scope,
good
functional
group
compatibility,
scalability
gram-scale
synthesis,
metal-
oxidant-free
conditions.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7571 - 7579
Опубликована: Май 17, 2023
Herein,
we
disclose
a
practical
and
simple
procedure
to
synthesize
2-aminobenzoxaoles.
Simple
anilines
formamides
were
used
as
substrates.
The
C–H
bond
ortho
the
amino
group
in
was
directly
functionalized
under
cobalt-catalyzed
conditions
with
high
levels
of
functional
tolerance.
Hypervalent
iodine(III)
both
an
oxidant
Lewis
acid
for
this
reaction.
mechanism
study
showed
that
transformation
may
involve
radical
process.
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
13(8)
Опубликована: Июнь 4, 2024
Abstract
A
straightforward
strategy
for
the
synthesis
of
pharmaceutically
active
2‐aminobenzoxazoles
and
2‐aminobenzothiazoles
is
described
by
using
2‐aminophenols,
2‐aminothiophenols,
functionalized
phenylisothiocyanates
as
model
substrates.
The
developed
method
proceeds
through
HFIP‐promoted
cyclodesulfurization
process
which
allows
efficient
these
scaffolds
at
60
°C
reaction
temperature
without
addition
a
transition
metal‐catalyst
or
hazardous
solvents
with
excellent
yields
(up
to
92
%)
product
formation.
This
involves
HFIP‐mediated
hydrogen
bonding
interactions
hydroxyl
thiol
moieties,
leading
bond
breaking
formation
during
reaction,
resulting
in
compounds
interest
situ
release
H
2
S
gas.
Molecules,
Год журнала:
2025,
Номер
30(2), С. 319 - 319
Опубликована: Янв. 15, 2025
Oxazole,
a
versatile
and
significant
heteroarene,
serves
as
bridge
between
synthetic
organic
chemistry
applications
in
the
medicinal,
pharmaceutical,
industrial
fields.
Polycyclic
aromatic
compounds
with
amino
groups
substituted
at
2-position
of
an
oxazole,
such
2-aminonaphthoxazoles,
are
expected
to
be
functional
probes,
but
their
methods
extremely
limited.
Herein,
we
describe
electrochemical
reactions
3-amino-2-naphthol
or
3-amino-2-anthracenol
isothiocyanates
DMSO,
using
graphite
electrode
anode
platinum
cathode
presence
potassium
iodide
(KI),
which
afford
N-arylnaphtho-
N-arylanthra[2,3-d]oxazol-2-amines
via
cyclodesulfurization.
This
reaction
is
first
example
synthesis
2-aminoxazole-based
polycyclic
reaction.
An
examination
spectroscopic
properties
oxazoles
revealed
that
λabs
value
tetracyclic
was
redshifted
relative
tricyclic
oxazoles.
Moreover,
synthesized
naphthalene/anthracene-fused
exhibited
extended
π-conjugated
skeletons
fluoresced
340–430
nm
region
chloroform.
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 28, 2025
Comprehensive
Summary
Chiral
tricyclic
compounds
represent
a
significant
class
of
biologically
active
substances
with
wide‐ranging
applications
in
materials
science,
medicinal
chemistry,
as
well
the
food
and
fragrance
industries.
Here,
we
combine
CAST
(combinatorial
site
saturation
test)
bacterial
surface
display
technology
to
develop
laboratory‐evolved
whole‐cell
catalyst,
designated
SD‐VHb
Tric
(surface
vitreoscilla
hemoglobin).
This
novel
carbene‐transferase
is
based
on
engineered
VHb
employs
strategy
for
cyclopropanation
unsaturated
π‐systems
synthesize
various
chiral
structures.
exhibits
unparalleled
stereocontrol
(up
99.9%
de
99%
ee
)
good
reactivity,
enabling
synthesis
structures
diverse
aromatic
or
heterocyclic
ring
scaffolds
from
simple
starting
materials.
Additionally,
computational
studies
were
conducted
elucidate
crucial
role
intermolecular
hydrophobic
interactions
regulating
reaction,
while
also
demonstrating
impact
adaptive
changes
pocket
size
orientation
ligand.
