Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
366(2), P. 269 - 276
Published: Nov. 30, 2023
Abstract
Here
we
present
a
[3+2]
cycloaddition
of
rationally
designed
trisubstituted
cyclic
α‐chloroamides,
primarily
those
incorporating
pharmacological
pyrazolone
cores,
as
potent
synthons
for
synthesizing
valuable
spirocyclic
γ‐lactam
architectures.
This
protocol
exhibits
52–96%
yields,
impressive
substrate
compatibility,
and
scale‐up
capacity.
Importantly,
this
study
also
represents
one
the
rare
examples
that
harness
enaminone
C−N
bond
cleavage
to
engineer
relevant
skeletons
biological
interest.
Moreover,
propose
plausible
mechanistic
explanation
elucidate
outstanding
chemical
outcomes
observed,
thereby
enriching
synthetic
toolbox
chemistry
α‐haloamide‐mediated
reactions.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(18), P. 4474 - 4487
Published: Jan. 1, 2023
Photogenerated
ketenes
simplify
and
accelerate
the
synthesis
of
diverse
cyclic
architectures
demonstrate
their
promising
applications
in
flow
chemistry.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(19), P. 13427 - 13439
Published: Sept. 26, 2023
Herein,
a
series
of
chiral
δ-lactam
frameworks
have
been
synthesized
and
catalyzed
by
phosphoric
acid
(CPA)
utilizing
two
kinds
open-chain
aza-dienes
azlactones
derived
from
amino
acids.
This
powerful
[4
+
2]
annulation
produces
broad
substrate
scope
with
functional
group
tolerance
in
yield
up
to
97%
98:2
er.
Moreover,
facile
scale-up
straightforward
conversion
diversely
substituted
products
verify
the
synthetic
utility
this
method
featuring
good
compatibility
high
efficiency.
Synthesis,
Journal Year:
2024,
Volume and Issue:
unknown
Published: July 18, 2024
Abstract
Spirocyclic
β-lactams
are
a
family
of
natural
and
synthetic
chemicals
with
different
biological
activities,
including
antibacterial
properties,
interact
critical
physiological
targets
such
as
T-type
calcium
channels
acetyl-CoA
cholesterol
acyltransferase.
Their
unique
chemical
structure,
combining
spiro
ring
system
β-lactam
group,
offers
promising
opportunities
for
the
targeted
discovery
medications
in
medicinal
chemistry.
have
potential
to
be
adaptable
frameworks
developing
novel
therapeutic
medicines
particular
three-dimensional
pharmacophoric
characteristics
increased
efficacy.
Numerous
methods
employed
synthesis
spirocyclic
β-lactams,
cyclization,
functional
group
modifications,
asymmetric
utilizing
chiral
catalysts
biomimetic
approaches.
In
this
short
review,
two
distinct
approaches
describing
recent
syntheses
(from
2021
2024)
discussed.
The
first
is
based
on
constructing
ring,
while
other
entails
transforming
monocyclic
into
structures.
These
include
detailed
reaction
processes
descriptions
functions
target
spirocycles.
applications
chemistry
highlight
their
role
structurally
diverse
compounds
significant
potential,
demonstrating
creative
building
complex
molecular
1
Introduction
2
β-Lactam
Ring
Synthesis
3
Non-β-Lactam
4
Miscellaneous
Examples
5
Conclusion
Outlook
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(22), P. 4548 - 4558
Published: Oct. 8, 2024
Abstract
The
synthesis
of
β‐lactam
scaffolds
is
paramount
importance
due
to
their
extensive
applications
in
pharmaceuticals,
particularly
as
antibiotics.
Visible
light
photocatalysis
has
emerged
a
revolutionary
approach
this
domain,
providing
sustainable
and
efficient
pathway
for
construction.
In
review,
we
meticulously
discuss
the
recent
developments
photocatalysed
frameworks.
A
key
focus
Staudinger
reaction,
traditionally
cornerstone
synthesis,
its
adaptation
visible
photocatalysis.
We
explore
mechanistic
intricacies
reaction
under
photochemical
conditions,
along
with
other
pivotal
cyclization
strategies
enabled
by
light.
By
illuminating
novel
photocatalytic
routes
β‐lactams,
review
provides
thorough
understanding
state‐of‐the‐art
techniques
sets
stage
future
innovations
green
these
critical
compounds.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(35), P. 7106 - 7114
Published: Jan. 1, 2023
An
efficient
visible-light-induced
Staudinger
[2
+
2]
annulation
reaction
between
α-diazo
ketones
and
dibenzo[b,f][1,4]oxazepine/thiazepine-imines
under
catalyst-free
conditions
has
been
developed.
This
protocol
provides
a
facile
method
to
synthesize
tetracyclic
dibenzo[b,f][1,4]oxazepine/thiazepine-fused
β-lactams
bearing
quaternary
carbon
center
with
broad
substrate
scope
high
efficiency
(37
examples,
up
>99%
yield).
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(36), P. 7300 - 7304
Published: Jan. 1, 2023
An
efficient,
scalable
cascade
[1,5]
hydride
transfer/cyclization
approach
for
the
construction
of
spirocyclic
pyrazolone-pyrrolo[4,3,2-
de
]quinoline
skeletons
through
C(sp
3
)–H
functionalization.
Thermal Science and Engineering,
Journal Year:
2024,
Volume and Issue:
7(1), P. 5949 - 5949
Published: June 25, 2024
The
mechanism
is
investigated
for
Wolff
rearrangement/Staudinger
[2+2]
cycloaddition
cascade
and
Pd-catalyzed,
decarboxylative,
formal
[3+2]
cycloaddition.
rearrangement
of
3-diazotetramic
acid
determined
to
be
rate-limiting
step
generates
cyclic
acyl
ketene.
interaction
ketene
with
imine
firstly
results
in
zwitterion
followed
by
conrotatory
cyclization
giving
major
cis-β-lactam.
For
synthesis
s-VECs,
the
epoxidation−cyclization
hydrolysis
give
precursor
better
performing
exocyclic
derivative.
reaction
3-cyanochromone
includes
decarboxylation,
nucleophilic
attack
subsequent
ring
closure
yielding
5-exo-trig
furobenzopyranone.
Based
on
comparison
between
possible
paths,
diastereoselectivity
cis
over
trans
regio-divergence
7-endo-trig
are
both
kinetically
controlled
common.
positive
solvation
effect
suggested
decreased
absolute
activation
energies
chlorobenzene
chloroform
solution
compared
gas.
These
supported
Multiwfn
analysis
FMO
composition
specific
TSs,
MBO
value
vital
bonding,
breaking.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 25, 2024
Herein,
we
describe
a
diastereoselective
and
straightforward
synthetic
approach
to
polysubstituted
spirocyclic
bis-lactams
bearing
both
β-
γ-lactam
cores
with
diverse
substitution
patterns.
The
method
developed
is
based
on
microwave-assisted
Wolff
rearrangement/Staudinger
[2
+
2]
cycloaddition
sequence
involving
3-diazopiperidine-2,4-diones
imines.
corresponding
reaction
tolerates
wide
range
of
functionalities
in
substrates,
giving
the
target
generally
high
yields.
utility
thermally
promoted
rearrangement
has
been
extended
interaction
3-diazopiperidine-2,4-dione-derived
ketenes
various
nucleophiles
leading
derivatives
2-oxopyrrolidine-3-carboxylic
acids.
Our
findings
potentially
pave
an
avenue
for
designing
new
compounds
degree
medicinal
relevance
by
means
processes
studied.
