Synlett,
Journal Year:
2024,
Volume and Issue:
unknown
Published: March 14, 2024
Abstract
We
report
a
unique
synthetic
route
to
benzo[7]annulene
derivatives.
When
benzylidene
malonates
having
1-(N,N-dialkylamino)alkyl
group
at
the
ortho-position
are
treated
with
stoichiometric
amount
of
M(OTf)3
(M
=
Sc,
Yb,
Gd),
three
transformations
([1,4]-hydride
shift/isomerization
into
an
enamine/intramolecular
Stork
enamine
acylation)
proceed
sequentially
afford
various
derivatives
in
moderate
chemical
yields.
To
our
knowledge,
present
reaction
is
first
example
internal
redox
involving
[1,n]-hydride
shift/(n+3)-cyclization
process.
European Journal of Medicinal Chemistry,
Journal Year:
2024,
Volume and Issue:
275, P. 116556 - 116556
Published: June 5, 2024
Azepanes
or
azepines
are
structural
motifs
of
many
drugs,
drug
candidates
and
evaluated
lead
compounds.
Even
though
compounds
having
N-heterocyclic
7-membered
rings
often
found
in
nature
(e.g.
alkaloids),
the
natural
this
group
rather
rare
as
approved
therapeutics.
Thus,
recently
studied
azepane
azepine-congeners
predominantly
consist
semi-synthetically
synthetically-obtained
scaffolds.
In
review
a
comparison
drugs
investigated
leads
was
proposed
taking
into
regard
their
aspects
(stereochemistry),
biological
activities,
pharmacokinetic
properties
confirmed
molecular
targets.
The
N-heterocycles
reveal
wide
range
not
only
against
CNS
diseases,
but
also
e.g.
antibacterial,
anticancer,
antiviral,
antiparasitic
allergy
agents.
As
most
potential
structures,
belonging
to
N-heterocycles,
synthetic
scaffolds,
report
reveals
different
efficient
metal-free
cascade
approaches
useful
synthesize
both
simple
azepine-containing
congeners
those
oligocyclic
structures.
Stereochemistry
azepane/azepine
fused
systems,
view
data
binding
with
targets,
is
discussed.
Apart
from
we
compare
advances
SAR
studies
(mainly
2018
2023),
whereas
related
part
concerning
various
domino
strategies
focused
on
last
ten
years.
Organic Chemistry Frontiers,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
The
hydride
transfer-enabled
divergent
application
of
5-amino-isoxazoles
for
the
controllable
construction
diverse
tetrahydroquinolines
and
tetrahydroquinazolines
was
disclosed
with
employment
different
Lewis
acids.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(18), P. 5041 - 5052
Published: Jan. 1, 2022
This
review
highlights
the
encouraging
advances
in
hydride
transfer-involved
dearomatization
reaction
during
past
decade,
content
of
which
is
categorized
according
to
acceptors,
namely
vinylogous
imines
and
quinone
methides.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
26(1), P. 332 - 337
Published: Dec. 28, 2023
The
Brønsted
acid-controlled
switchable
synthesis
of
indoline-fused
tetrahydroquinolines
and
indole-fused
benzazepines
was
developed
through
hydride
transfer-enabled
formal
[5
+
1]
2]
cyclization
reactions
from
indoles
N-alkyl
o-aminobenzoketones.
Indoline,
furanone,
tetrahydroquinoline
hybridized
pentacyclic
products
were
unprecedentedly
accessed
via
a
cascade
condensation/hydride
transfer/dearomatization-cyclization/deethylation/nucleophilic
addition
process.
In
addition,
the
undeveloped
transfer-involved
cyclizations
also
realized
for
direct
construction
benzazepines.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(13), P. 5134 - 5141
Published: Jan. 1, 2023
The
H
2
O-promoted
controllable
synthesis
of
diverse
3-carboxyl
and
3-acyl
substituted
tetrahydroquinolines
3,4-dihydroquinolin-2(1
)-ones
from
readily
available
feedstocks
was
developed
by
a
hydride
transfer
strategy.
Molecules,
Journal Year:
2024,
Volume and Issue:
29(17), P. 4241 - 4241
Published: Sept. 6, 2024
Xanthones
are
chemical
substances
in
higher
plants,
marine
organisms,
and
lower
microorganisms.
The
most
prevalent
naturally
occurring
sources
of
xanthones
those
belonging
to
the
families
Caryophyllaceae,
Guttiferae,
Gentianaceae.
Structurally,
(9H
xanthan-9-one)
heterocyclic
compounds
with
oxygen
a
γ-pyrone
component.
They
densely
packed
two-benzene
ring
structure.
carbons
numbered
from
their
nucleus
biosynthetic
construct.
have
mixed
shikimate-acetate
(higher
plants)
acetate-malonate
(lower
organisms)
origins,
which
influence
classification.
Based
on
level
oxidation
C-ring,
they
classified
into
monomers,
dimers,
heterodimers.
While
based
oxygenation
or
type
residue,
can
be
categorized
mono-,
di-,
tri-,
tetra-,
penta-
hexa-oxygenated
xanthones,
bis-xanthones,
prenylated
related
xanthonolignoids,
other
miscellaneous
xanthones.
This
structural
diversity
has
made
exhibit
considerable
biological
properties
as
promising
antioxidant,
antifungal,
antimicrobial,
anticancer
agents.
Structure-activity
relationship
studies
suggest
C-1,
C-3,
C-6,
C-8
key
positions
that
activity
Furthermore,
presence
functional
groups,
such
prenyl,
hydroxyl,
glycosyl,
furan,
pyran,
at
may
contribute
spectrum
activity.
unique
scaffolds
notable
activities,
structure-activity
relationships
some
lead
molecules
were
discussed
identify
possible
drug
candidates.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(6), P. 1668 - 1674
Published: Jan. 1, 2022
The
dearomative
[5
+
1]
annulation
of
2-methylindoles
with
new
five-membered
synthon
was
developed
through
cascade
[1,5]-hydride
transfer/dearomative
cyclization
in
HFIP
for
the
synthesis
spirochromanes
bearing
2-methylindolenine
skeleton.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(18), P. 2991 - 3019
Published: July 14, 2023
Abstract
Propargylic
alcohols
are
readily
available
bifunctional
(alkyne
and
hydroxyl
groups)
synthons,
which
recognize
as
one
of
the
attractive
synthetic
feedstock
in
organic
transformations.
Especially,
recent
years
employment
these
valuable
molecules
has
frequently
been
observed
literature.
Hence,
present
review
highlights
advancements
application
propargylic
cyclization,
substitution,
addition
reactions.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(13), P. 3307 - 3312
Published: Jan. 1, 2023
An
unprecedented
example
of
skeletal
editing
pyrrolidines
to
1,2-oxazinanes
expands
the
applicability
scope
“single-atom”
skeletal-editing
technologies.
