Angewandte Chemie,
Год журнала:
2023,
Номер
135(40)
Опубликована: Авг. 16, 2023
Abstract
Axially
chiral
N
‐substituted
quinazolinones
are
important
bioactive
molecules,
which
presented
in
many
synthetic
drugs.
However,
most
strategies
toward
their
atroposelective
synthesis
mainly
limited
to
the
axially
arylquinazolinone
frameworks.
The
development
of
modular
methods
access
diverse
quinazolinone‐based
atropisomers
remains
scarce
and
challenging.
Herein,
we
report
regio‐
‐vinylquinazolinones
via
strategy
asymmetric
allylic
substitution‐isomerization.
catalysis
system
utilized
both
transition‐metal
organocatalysis
efficiently
afford
trisubstituted
tetrasubstituted
‐vinylquinazolinone
atropisomers,
respectively.
With
meticulous
design
β‐substituted
substrates,
Z
‐
E
‐tetrasubstituted
were
obtained
good
yields
high
enantioselectivities.
Chemical Reviews,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 13, 2024
Hypervalent
iodine(III)
compounds
have
found
wide
application
in
modern
organic
chemistry
as
environmentally
friendly
reagents
and
catalysts.
iodine
are
commonly
used
synthetically
important
halogenations,
oxidations,
aminations,
heterocyclizations,
various
oxidative
functionalizations
of
substrates.
Iodonium
salts
arylating
reagents,
while
iodonium
ylides
imides
excellent
carbene
nitrene
precursors.
Various
derivatives
benziodoxoles,
such
azidobenziodoxoles,
trifluoromethylbenziodoxoles,
alkynylbenziodoxoles,
alkenylbenziodoxoles
group
transfer
the
presence
transition
metal
catalysts,
under
metal-free
conditions,
or
using
photocatalysts
photoirradiation
conditions.
Development
hypervalent
catalytic
systems
discovery
highly
enantioselective
reactions
chiral
represent
a
particularly
recent
achievement
field
chemistry.
Chemical
transformations
promoted
by
many
cases
unique
cannot
be
performed
any
other
common,
non-iodine-based
reagent.
This
review
covers
literature
published
mainly
last
7-8
years,
between
2016
2024.
Chemical Communications,
Год журнала:
2023,
Номер
59(30), С. 4455 - 4458
Опубликована: Янв. 1, 2023
Herein,
we
demonstrate
a
regioselective
intramolecular
C-N
cross-coupling
for
the
synthesis
of
14H-quinazolino[3,2-f]phenanthridin-14-one
by
using
9-mesityl-10-methylacridinium
perchlorate
as
visible-light
(450-470
nm)
photocatalyst.
The
experiments
with
BHT,
TEMPO,
and
Stern-Volmer
quenching
studies
helped
to
rationalize
radical
pathway
via
SET
mechanism.
Organic Letters,
Год журнала:
2023,
Номер
25(22), С. 4075 - 4079
Опубликована: Май 26, 2023
Herein
we
have
developed
a
strategy
for
chemodivergent
functionalization
of
N-methylalkanamides
via
C-Br
bond
activation
CBr4,
using
an
orthorhombic
CsPbBr3
perovskite
photocatalyst
under
blue
LEDs
(450-470
nm).
The
selectivity
whether
5-exo-trig
spiro
cyclization
or
6-endo-trig
occurred
depended
on
the
stability
radical
intermediate
that
was
formed
after
addition
bromide
to
starting
compound
obtain
3,8-dibromo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-trien-2-on
3-bromo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
3-bromo-6-(tert-butyl)-1-methyl-4-phenylquinolin-2(1H)-one.
Organic Letters,
Год журнала:
2022,
Номер
24(43), С. 7912 - 7917
Опубликована: Окт. 21, 2022
3-(2-(Ethynyl)phenyl)quinazolinones
were
designed
and
synthesized
as
a
class
of
novel
efficient
skeletons
for
phosphorylation/cyclization
reactions.
Under
visible
light
irradiation,
series
phosphorylated
quinolino[2,1-b]quinazolinones
(35
examples,
up
to
87%
yield)
first
from
3-(2-(ethynyl)phenyl)quinazolinones
diarylphosphine
oxides
by
using
4CzIPN
photocatalyst
under
mild
conditions.
This
reaction
was
also
applicable
sunlight
irradiation.
Moreover,
the
efficiency
could
be
significantly
improved
continuous-flow
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(40)
Опубликована: Авг. 16, 2023
Abstract
Axially
chiral
N
‐substituted
quinazolinones
are
important
bioactive
molecules,
which
presented
in
many
synthetic
drugs.
However,
most
strategies
toward
their
atroposelective
synthesis
mainly
limited
to
the
axially
arylquinazolinone
frameworks.
The
development
of
modular
methods
access
diverse
quinazolinone‐based
atropisomers
remains
scarce
and
challenging.
Herein,
we
report
regio‐
‐vinylquinazolinones
via
strategy
asymmetric
allylic
substitution‐isomerization.
catalysis
system
utilized
both
transition‐metal
organocatalysis
efficiently
afford
trisubstituted
tetrasubstituted
‐vinylquinazolinone
atropisomers,
respectively.
With
meticulous
design
β‐substituted
substrates,
Z
‐
E
‐tetrasubstituted
were
obtained
good
yields
high
enantioselectivities.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(14), С. 10096 - 10110
Опубликована: Июль 3, 2023
Herein
we
report
a
cascaded
chalcogenation
of
aryl
alkynoates
or
N-arylpropynamides
using
9-mesityl-10-methylacridinium
perchlorate
as
visible
light
photocatalyst
to
obtain
selectively
either
3-sulfenylated/selenylated
coumarins
spiro[4,5]trienones.
In
radical
initiated
process,
the
spiro-cyclization
reaction
was
favored
due
presence
-OMe
-F
substituent
at
para
position
group,
which
helped
stabilize
allylic
intermediate
formed
during
reaction.
Otherwise,
6-endo-trig
cyclization
led
coumarins.
Overall,
new
C–S/C–Se,
C–C,
and
C═O
bonds
were
in
single
step.
The
Stern–Volmer
quenching
study,
EPR
experiments,
ON-OFF
trapping
etc.,
understand
radical-based
mechanism.
Chemistry - An Asian Journal,
Год журнала:
2024,
Номер
19(14)
Опубликована: Май 8, 2024
The
beginning
of
photochemical
reactions
revolutionized
synthetic
chemistry
through
sustainable
practices.
This
review
explores
cutting-edge
developments
in
leveraging
light-induced
processes
for
generating
cascaded
C-C
and
C-hetero
bonds
without
catalysts.
Significantly,
catalyst-free
photoinduced
methodologies
have
garnered
considerable
attention,
especially
the
creation
varied
heterocyclic
frameworks
drug
design
synthesis
natural
products.
article
delves
into
underlying
mechanisms,
addresses
limitations,
evaluates
various
methodologies,
emphasizing
potential
photocatalyst
transition
metal-free
to
enhance
sustainability.
Divided
two
sections,
it
covers
recent
strides
C-heteroatom
multiple
bond
formation
reactions.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(8), С. 1863 - 1876
Опубликована: Фев. 21, 2024
Abstract
Ru(II)‐catalyzed
and
solvent‐switched
[3+2]‐spiroannulation
[4+n]
(n=1,
2,
3)
annulations
of
2‐aryl
quinazolinone
or
2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones
with
ynones
alkynyl
alcohol
1,3‐diynes
under
mild
reaction
conditions
have
been
analyzed.
These
reactions
take
place
in
the
presence
appropriate
solvent
features
a
redox‐neutral
pathway.
Ynone
serves
as
an
‘atypical
one‐carbon
unit’
[4+1]
annulation
generates
tetrasubstituted
carbon
center
bearing
diverse
heterocycles
through
[3+2]
strategies.
Post
transformations
synthesized
spiro‐products
augments
potential
developed
methodology.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(11), С. 2456 - 2460
Опубликована: Март 21, 2024
Abstract
An
iron(II)‐catalyzed
cascade
reaction,
involving
cyanoalkylsulfonylation
and
cyclization,
has
been
devised
to
enable
the
synthesis
of
functionalized
sulfonylated
quinolino‐quinazolinone
alkyl
nitriles.
This
three‐component
radical
transformation
exhibits
excellent
chemo‐
regioselectivity
while
functioning
without
need
for
external
oxidizing
or
reducing
agents.
The
cost‐effectiveness
this
catalytic
system,
together
with
its
broad
substrate
application,
which
includes
drug
molecule
derivatives,
make
approach
efficient
adaptable.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(9), С. 2035 - 2043
Опубликована: Фев. 8, 2024
Abstract
Our
research
has
demonstrated
that
mechanochemical
activation
is
more
effective
with
solid
reagents.
We
have
showcased
the
practicality
of
Bertagnini's
salts,
also
called
aldehyde‐bisulfite
adducts,
which
are
crystalline,
simplifying
preparation
and
storage.
These
salts
stable
substitutes
for
liquid
aldehydes
ketones
been
employed
in
reductive
amination,
synthesizing
aza‐heterocycles
hydrazones
within
mechanochemistry.
The
technique‘s
effectiveness
broadens
substrate
scopes,
simplifies
purification,
reduces
reaction
times,
yields
desired
products
ranging
from
38–91%.
Additionally,
thermal
stability
bisulfite
adducts
confirmed
through
TGA
(Thermogravimetric
analysis)
analysis.
