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.
Angewandte Chemie,
Год журнала:
2024,
Номер
136(48)
Опубликована: Авг. 22, 2024
Abstract
Over
the
past
few
years,
there
has
been
a
surge
of
interest
in
chemistry
bicyclobutanes
(BCBs).
Although
BCBs
have
used
to
synthesize
bicyclo[2.1.1]hexanes
and
bicyclo[3.1.1]heptanes,
synthesis
bicyclo[4.1.1]octanes
remained
elusive.
Herein,
we
report
first
Lewis
acid‐catalyzed
unexpected
(4+3)
annulation
para
‐quinonemethides
(
p
‐QMs)
with
allowing
oxabicyclo[4.1.1]octanes
proceeding
under
mild
conditions.
With
5
mol
%
Bi(OTf)
3
,
reaction
afforded
annulated
product
high
regioselectivity
good
functional
group
compatibility
via
simultaneous
acid
activation
‐QMs.
The
is
likely
initiated
by
1,6‐addition
activated
‐QMs
followed
C2‐selective
intramolecular
addition
phenol
moiety
generated
cyclobutyl
cation
intermediate.
Moreover,
detailed
mechanistic
studies
provided
insight
into
mechanism
reaction.
Abstract
Bicyclo[1.1.1]pentane
(BCP)
is
a
bridging
ring
skeleton
with
three-dimensional
structure.
BCP
bioisostere
of
the
phenyl
ring,
tert-butyl
group,
and
alkynes;
it
has
excellent
physical
chemical
properties
compared
so
been
widely
considered
by
pharmaceutical
chemistry.
This
short
review
examines
related
reports
as
changes
in
physicochemical
biological
activity
after
substitution.
The
solubility,
clogP,
metabolic
toxicity
drug
are
improved
bioisosteres,
but
lower
than
ring.
application
research
development
will
be
further
expanded
to
provide
more
possibilities
for
future
innovation
development.
1
Introduction
2
Replacement
Phenyl
Rings
3
Conclusion
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.
