Molecules,
Год журнала:
2023,
Номер
28(15), С. 5734 - 5734
Опубликована: Июль 28, 2023
An
oxidant-free
and
highly
efficient
synthesis
of
phenolic
quinazolin-4(3H)-ones
was
achieved
by
simply
stirring
a
mixture
2-aminobenzamides,
sulfonyl
azides,
terminal
alkynes.
The
intermediate
N-sulfonylketenimine
underwent
two
nucleophilic
additions
the
group
eliminated
through
power
aromatization.
natural
product
2-(4-hydroxybenzyl)quinazolin-4(3H)-one
can
be
synthesized
on
large
scale
under
mild
conditions
with
this
method.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(4), С. 1169 - 1174
Опубликована: Дек. 29, 2023
A
catalyst-free,
photoinduced
three-component
reaction
involving
sulfur
dioxide
insertion/sulfonyl
radical
addition
to
an
unactivated
CC
double
bond/Minisci-type
cyclization
sequence
has
been
developed
access
sulfonated
quinazolinones.
The Chemical Record,
Год журнала:
2023,
Номер
24(2)
Опубликована: Окт. 13, 2023
Quinazolin-4-one,
its
heteroanalogues,
and
derivatives
represent
an
outstandingly
important
class
of
compounds
in
modern
organic,
medicinal,
pharmaceutical
chemistry,
as
these
molecular
structures
are
noted
for
their
wide
synthetic
pharmacological
potential.
In
the
last
years,
ever-increasing
research
attention
has
been
paid
to
quinazolinone
bearing
alkenyl
alkynyl
substituents
on
pyrimidinone
nucleus.
The
original
structural
combination
synthetically
powerful
endocyclic
amidine
(or
amidine-related)
exocyclic
unsaturated
moieties
provides
a
driving
force
cyclizations,
which
offer
efficient
toolkit
construct
variety
fused
pyrimidine
systems
with
saturated
N-
N,S-heterocycles.
this
connection,
present
review
article
is
mainly
aimed
at
systematic
coverage
progress
using
alkenyl(alkynyl)quinazolinones
heteroanalogues
convenient
bifunctional
substrates
regioselective
annulation
small-
medium-sized
heterocyclic
nuclei.
Much
elucidating
electronic
effects
reagents
regio-
stereoselectivity
cyclizations
well
clarifying
relevant
reaction
mechanisms.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(46), С. 9112 - 9122
Опубликована: Янв. 1, 2023
Organic
thiocyanates
are
valuable
biological
moities
and
drug-building
blocks.
They
can
also
transform
effectively
into
thioethers,
thiols,
alkynyl
thiocarbamates
in
synthetic
chemistry.
With
respect
to
the
merits
of
thiocyanates,
many
chemists
our
research
team
have
developed
diverse
strategies
access
SCN-revised
heterocycles/spirocycles
via
an
effective
radical
cyclization
process.
Hence,
this
review
article
first
describes
importance/application
thiocyanates.
Subsequently,
it
summarizes
reaction
conditions,
substrate
scopes,
plausible
mechanism,
respectively,
excellent
work
stated
above.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(17)
Опубликована: Март 19, 2024
Abstract
Herein,
we
reported
a
selective,
mild
method
for
the
visible‐light‐photocatalyzed
trifluoromethylation
and
cyclization
of
unactivated
tethered
alkenes
to
provide
tri‐
tetracyclic
quinazolinones.
Trifluoroacetic
acid
anhydride
are
inexpensive
readily
available
reagents
process
that
proceeds
without
addition
strong
oxidant.
The
wide
substrate
scope
formation
5‐
6‐membered
rings
demonstrated
in
44–82
%
yields.
Control
experiments
basis
proposed
mechanism
involving
photocatalyzed
SET
from
fac
‐Ir(ppy)
3
TFAA
trifluoromethyl
radical‐mediated
regioselective
cyclization.
practicality
protocol
was
illustrated
by
gram‐scale
synthesis
76
yield.
New
photochemical
approaches
to
2,3-fused
quinazolinones
and
dihydroquinazolinones
are
disclosed.
The
intramolecular
hydrocyclization
proceeds
in
moderate
excellent
yields
across
diverse
alkenes
with
high
regioselectivity
diastereocontrol.
Mechanistic
studies
indicated
that
the
radical
cascade
processes
involve
thiophenol
acting
as
single-electron
transfer
hydrogen
atom
reagents.
success
of
gram-scale
synthesis
proves
strategy
can
be
used
for
practical
applications.
Catalysts,
Год журнала:
2023,
Номер
13(6), С. 1007 - 1007
Опубликована: Июнь 14, 2023
A
novel
metal-free
photoredox-catalyzed
cyclization
reaction
of
N-aryl
acrylamide
is
herein
reported
that
provides
synthetically
valuable
oxindole
derivatives
through
the
bis-mediation
H2O
and
aldehyde.
In
this
work,
sustainable
visible
light
was
used
as
energy
source,
organic
light-emitting
molecule
4CzIPN
served
efficient
photocatalyst.
The
main
characteristics
are
environmentally
friendly
high
yields.
Abstract
The
synthesis
of
acylmethylatated
pyrrolo‐quinazolinones
was
developed
via
photo‐induced
cascade
radical
addition/cyclization
N
‐(but‐3‐enyl)quinazolin‐4(3
H
)‐ones
with
sulfoxonium
ylides
using
4CzIPN
as
the
photocatalyst.
This
approach
also
suitable
for
construction
piperidino‐quinazolinones.
protocol
features
mild
conditions,
convenient
operation,
broad
substrate
scope
and
good
functional
group
compatibility.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(21), С. 6019 - 6025
Опубликована: Янв. 1, 2024
A
visible-light-induced
intermolecular
silylation
and
hydrolipocyclization
using
hydrosilane
as
the
hydrogen
silicon
source
has
been
developed,
which
provided
an
efficient
pathway
for
synthesis
of
organosilanes
polycyclic
quinazolinones.
