Divergent Synthesis of Sulfur‐Containing Bridged Cyclobutanes by Lewis Acid Catalyzed Formal Cycloadditions of Pyridinium 1,4‐Zwitterionic Thiolates and Bicyclobutanes
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
unknown
Опубликована: Май 31, 2024
Bridged
cyclobutanes
and
sulfur
heterocycles
are
currently
under
intense
investigation
as
building
blocks
for
pharmaceutical
drug
design.
Two
formal
cycloaddition
modes
involving
bicyclobutanes
(BCBs)
pyridinium
1,4-zwitterionic
thiolate
derivatives
were
described
to
rapidly
expand
the
chemical
space
of
sulfur-containing
bridged
cyclobutanes.
By
using
Ni(ClO
Язык: Английский
Divergent Synthesis of Sulfur‐Containing Bridged Cyclobutanes by Lewis Acid Catalyzed Formal Cycloadditions of Pyridinium 1,4‐Zwitterionic Thiolates and Bicyclobutanes
Angewandte Chemie,
Год журнала:
2024,
Номер
136(40)
Опубликована: Май 31, 2024
Abstract
Bridged
cyclobutanes
and
sulfur
heterocycles
are
currently
under
intense
investigation
as
building
blocks
for
pharmaceutical
drug
design.
Two
formal
cycloaddition
modes
involving
bicyclobutanes
(BCBs)
pyridinium
1,4‐zwitterionic
thiolate
derivatives
were
described
to
rapidly
expand
the
chemical
space
of
sulfur‐containing
bridged
cyclobutanes.
By
using
Ni(ClO
4
)
2
catalyst,
an
uncommon
higher‐order
(5+3)
BCBs
with
quinolinium
was
achieved
broad
substrate
scope
mild
reaction
conditions.
Furthermore,
first
Lewis
acid‐catalyzed
asymmetric
polar
BCB
pyridazinium
accomplished.
In
contrast,
thiolates
undergo
Sc(OTf)
3
‐catalyzed
(3+3)
generate
thia‐norpinene
products,
which
represent
initial
instance
synthesizing
2‐thiabicyclo[3.1.1]heptanes
(thia‐BCHeps)
from
BCBs.
Moreover,
we
have
successfully
used
this
protocol
prepare
thia‐BCHeps‐substituted
analogues
bioactive
molecule
Pitofenone.
Density
functional
theory
(DFT)
computations
imply
that
kinetic
factors
govern
between
thiolate,
whereas
is
thermodynamic
control.
Язык: Английский
Rapid construction of S-containing spirooxindoles and dispirooxindoles via annulation of MBH maleimides of isatins
Tetrahedron Letters,
Год журнала:
2025,
Номер
156, С. 155452 - 155452
Опубликована: Янв. 13, 2025
Язык: Английский
I2-Induced Umpolung: Synthesis of a 1,6-Dihydrofuro[3,2-b]pyrazolo[3,4-e][1,4]thiazine Skeleton via an Unconventional 1,4-Dithiane-2,5-diol Reaction Mode
Zhi‐Cheng Yu,
Kai‐Lu Zheng,
Xi Shen
и другие.
Organic Letters,
Год журнала:
2024,
Номер
26(37), С. 7891 - 7896
Опубликована: Сен. 6, 2024
In
this
paper,
novel
sulfur-containing
1,6-dihydrofuro[3,2-
Язык: Английский
Assembly of Thiazino[3,4‐a]isoquinoline and Thiazepino[5,4‐a]isoquinoline Frameworks from Isoquinolinium 1,4‐Zwitterionic Thiolates via [5 + 1] and [5 + 2] Cycloaddition Reactions
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 18, 2024
Abstract
Two
cycloaddition
modes
of
isoquinolinium
1,4‐zwitterionic
thiolates
have
been
established.
Upon
choosing
α
‐bromo
ketones
as
the
counterpart,
a
range
isoquinoline‐fused
thiazines
can
be
attained
with
yields
ranging
from
moderate
to
excellent
through
formal
[5+1]
reaction
pathway,
exhibiting
remarkable
substrate
adaptability
and
resilience
diverse
functional
groups.
Additionally,
library
unprecedented
thiazepino[5,4‐
]isoquinolines,
novel
category
seven‐membered
heterocycles,
has
synthesized
via
[5+2]
pathway
utilizing
acetylenedicarboxylate
reactive
component.
Notably,
this
process
stands
out
for
its
exceptional
100
%
atomic
utilization
efficiency.
Язык: Английский
Design, synthesis and evaluation of structurally diverse polycyclic harmaline scaffolds as anticancer agents
New Journal of Chemistry,
Год журнала:
2024,
Номер
48(14), С. 6322 - 6334
Опубликована: Янв. 1, 2024
This
is
the
first
example
of
harmaline
scaffolds
as
acceptor/acceptor-based
N–C–C
synthons
and
evaluation
3at
an
anticancer
agent.
Язык: Английский
Ruthenium-Catalyzed Interrupted Transfer Hydrogenation: An Approach for Reductive Functionalization of Quinolinium and Napthyridinium Salts
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(18), С. 13167 - 13178
Опубликована: Сен. 11, 2024
Until
now,
a
myriad
of
effective
approaches
have
emerged
for
the
functionalization
Язык: Английский
Synthesis of 4-Hydroxyindolin-2-ones via Phosphoric Acid-Mediated Annulation of β-Nitrostyrenes with 1,3-Cyclohexanedione
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 12, 2024
The
efficient
synthesis
of
4-hydroxy-3-arylindolin-2-ones
via
phosphoric
acid-mediated
annulation
various
β-nitrostyrenes
and
1,3-cyclohexanedione
is
described.
This
reaction
gives
a
practical
method
for
affording
diverse
set
oxindoles,
having
simple
experimentation,
readily
available
starting
materials,
very
good
yields.
Additionally,
substituted
1,3-cyclohexanediones
under
the
same
conditions
afforded
tetrahydrobenzofuran
oxime
compounds.
Язык: Английский