Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
366(2), С. 241 - 247
Опубликована: Ноя. 24, 2023
Abstract
The
established
strategy
unveils
a
metal
and
mediator‐free
electrochemical
[3+2]
cycloaddition
approach
among
α
‐amino
carbonyls
tosylmethyl
isocyanide
(TosMIC)
fabricating
substituted
imidazole
scaffolds.
Implementation
of
electro‐redox
conditions
on
this
eliminates
the
essential
requirement
transition
catalysts
chemical
oxidants.
A
wide
variety
different
functionalities
are
well
tolerated
under
reaction
condition,
contributing
to
substrate
scope
applicability.
Several
control
experiments
cyclic
voltammetry
studies
suggest
an
electro‐oxidation
triggered
successive
C−C
C−N
bond
formations
followed
by
rapid
aromatization
for
constructing
five‐membered
core
structure.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8420 - 8434
Опубликована: Июнь 5, 2024
An
elegant
and
highly
concise
strategy
for
the
construction
of
coumarin-functionalized
pyrrolo[2,1-a]isoquinolines
from
available
propargylamines
isoquinolinium
N-ylides
has
been
disclosed.
In
this
reaction,
acted
as
a
C2
synthon
to
form
coumarin
ring
well
1,3-dipole
construct
pyrrole
in
single
pot.
This
cascade
process
involves
1,4-conjugate
addition/lactonization/1,3-dipolar
cycloaddition
four
chemical
bonds
(one
C–O
bond
three
C–C
bonds)
two
new
heterocyclic
skeletons.
Additionally,
most
these
compounds
showed
good
fluorescence
properties
exhibited
high
molar
extinction
coefficient
large
Stokes
shifts.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(7), С. 4649 - 4661
Опубликована: Март 22, 2023
We
have
successfully
modified
a
series
of
pyrrolo[2,1-a]isoquinolines
via
direct
nitration
under
mild
reaction
conditions.
Easily
accessible
nitrates
including
CAN,
Cu(NO3)2·H2O,
and
Fe(NO3)3·9H2O
all
can
serve
as
effective
nitrating
reagents
for
functionalizing
pyrrolo[2,1-a]isoquinolines.
Various
nitro-bearing
been
efficiently
prepared
in
acceptable
to
good
yields.
Organic Letters,
Год журнала:
2023,
Номер
25(26), С. 4908 - 4912
Опубликована: Июнь 23, 2023
A
decarboxylative/dehydrofluorinative
formal
[3
+
2]
cycloaddition
aromatization
of
isoquinolinium
N-ylides
with
difluoroenoxysilanes
has
been
developed.
This
methodology
provides
a
facile
and
straightforward
synthetic
pathway
to
afford
highly
functionalized
fluorinated
pyrrolo[2,1-a]isoquinolines
in
good
excellent
yields
under
mild
conditions.
Moreover,
gram-scale
derivatization
experiments
for
the
late-stage
functionalization
drug
molecules
have
also
demonstrated.
Molecules,
Год журнала:
2024,
Номер
29(17), С. 4032 - 4032
Опубликована: Авг. 26, 2024
Lamellarins
are
natural
products
with
a
[3,4]-fused
pyrrolocoumarin
skeleton
possessing
interesting
biological
properties.
More
than
70
members
have
been
isolated
from
diverse
marine
organisms,
such
as
sponges,
ascidians,
mollusks,
and
tunicates.
There
is
continuous
interest
in
the
synthesis
of
these
compounds.
In
this
review,
synthetic
strategies
for
title
compounds
presented
along
their
Three
routes
followed
lamellarins.
Initially,
pyrrole
derivatives
starting
or
intermediate
compounds,
then
they
fused
to
isoquinoline
coumarin
moiety.
Second,
compound
an
indole
last
route,
coumarins
which
moiety
scaffold.
The
isolamellarins,
azacoumestans,
isoazacoumestans,
analogues
also
described.
above
achieved
via
metal-catalyzed
cross-coupling,
[3
+
2]
cycloaddition,
substitution,
lactonization
reactions.
exhibit
cytotoxic,
multidrug
resistance
(MDR),
topoisomerase
I-targeted
antitumor,
anti-HIV,
antiproliferative,
anti-neurodegenerative
disease,
anti-inflammatory
activities.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(5), С. 2822 - 2831
Опубликована: Фев. 10, 2023
A
mild
bromination
of
pyrrolo[2,1-a]isoquinolines
has
been
achieved
using
acetyl
bromide
and
dimethyl
sulfoxide.
series
brominated
could
be
obtained
in
moderate
to
excellent
yields
(46-99%)
at
room
temperature.
This
strategy
can
also
expanded
the
facile
polysubstituted
pyrroles,
indoles,
electron-rich
phenols,
aniline,
2-naphthol.
We
report
a
visible-light
photoredox-induced
stereoselective
radical
1,3-dipolar
cycloaddition
between
tetrahydroisoquinolines
and
coumarin
derivatives,
providing
platform
for
the
efficient
synthesis
of
pseudo-natural-inspired
fused
pentacyclic
scaffolds.
Using
this
protocol,
diverse
range
valuable
pyrrolo[2,1-a]isoquinolines
were
efficiently
obtained
in
moderate
to
good
yields
excellent
diastereoselectivities.
Mechanistic
investigations
including
control
experiments
light
on/off
studies
indicated
that
reaction
underwent
induced
process.
The
insights
gained
from
our
are
expected
advance
general
efforts
toward
green
biology-oriented
pseudo-natural
products
heterocyclic
skeletons.
