Electrochemical Synthesis of 2-Amino-1,3-benzoxazines via TBAI-mediated Desulfurative Cyclization of Isothiocyanates and 2-Aminobenzyl Alcohols
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.
Язык: Английский
Synthesis and Optical Properties of N-Arylnaphtho- and Anthra[2,3-d]oxazol-2-amines
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.
Язык: Английский
Organocatalytic Approaches towards the Synthesis of Asymmetric Tetrahydroquinoline (THQ) Derivatives
Synthesis,
Год журнала:
2024,
Номер
unknown
Опубликована: Июль 30, 2024
Abstract
1,2,3,4-Tetrahydroquinolines
(THQs)
are
present
in
molecules
with
significant
biological
importance
and
pharmaceuticals
diverse
activities.
Various
synthetic
routes
have
been
developed
to
tetrahydroquinolines,
such
as
the
hydrogenation
of
quinolines,
domino
reactions,
intramolecular
cyclization,
notably,
Povarov
reaction.
Organocatalysts
small,
chiral
organic
that
can
successfully
catalyze
transformations.
This
review
examines
use
organocatalysts
asymmetric
synthesis
tetrahydroquinoline
derivatives
using
aminocatalysis,
NHC
catalysis,
H-bonding
catalysis
covering
literature
between
2000
early
2024.
1
Introduction
2
Aminocatalysis
3
Catalysis
4
H-Bonding
5
Miscellaneous
6
Conclusion
Язык: Английский