Synthesis,
Год журнала:
2021,
Номер
53(15), С. 2545 - 2558
Опубликована: Март 24, 2021
Abstract
Organochalcogen-containing
cyclic
molecules
have
shown
several
promising
pharmacological
properties.
Consequently,
different
strategies
been
developed
for
their
synthesis
in
the
past
few
years.
Particularly
due
to
low
cost
and
environmental
aspects,
copper-
iron-promoted
cyclization
reactions
of
alkynyl
substrates
broadly
efficiently
applied
this
purpose.
This
short
review
presents
an
overview
most
recent
advances
organochalcogen-containing
carbo-
heterocycles
by
reacting
diorganyl
disulfides,
diselenides,
ditellurides
with
alkyne
derivatives
presence
copper
iron
salts
promote
reactions.
1
Introduction
2
Synthesis
Carbo-
Heterocycles
via
Reactions
Alkynes
Diorganyl
Dichalcogenides
Copper
Salts
3
Iron
4
Conclusions
Organic Letters,
Год журнала:
2022,
Номер
24(3), С. 859 - 863
Опубликована: Янв. 12, 2022
Herein
a
novel
and
concise
approach
to
pyrrole
skeletons
via
Pd-catalyzed
tandem
cyclization
reactions
is
investigated.
The
substrates
for
the
transformation
could
be
readily
prepared
by
phosphoric
acid-catalyzed
Ugi
with
available
starting
materials.
In
this
strategy,
two
isocyanides
participate
in
sequential
isocyanide
insertion
reactions,
chemoselectivity
of
products
regulated
steric
hindrance
isocyanide.
A
plausible
mechanism
formation
corresponding
adducts
proposed.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(13), С. 3252 - 3258
Опубликована: Янв. 1, 2023
A
novel
one-pot
method
for
synthesizing
polysubstituted
pyrrole
derivatives
via
three-component
reactions
of
alkenyl
bromides,
amines,
and
isocyanides
is
reported
by
Pd
catalysis,
without
additional
ligands,
with
the
orderly
insertion
three
isocyanide
molecules.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 10, 2025
Compared
with
the
well-developed
cyclization
of
functionalized
propargylamines,
use
unactivated
tertiary
propargylamines
to
access
pyrroles
remains
challenging.
Herein,
we
report
an
efficient
method
for
constructing
tetrasubstituted
via
a
DBU-mediated
intramolecular
cycloaddition
N-alkyl
propargylamines.
This
reaction
employs
dihydropyrrole
intermediates,
followed
by
oxidation
produce
in
presence
2,3-dichloro-5,6-dicyano-p-benzoquinone.
In
addition,
broad
substrate
scope,
high
atom
economy,
selectivity,
and
simple
operation
are
also
advantages
this
protocol.
Organic & Biomolecular Chemistry,
Год журнала:
2020,
Номер
18(26), С. 4906 - 4915
Опубликована: Янв. 1, 2020
This
review
deals
with
the
methodologies
published
in
last
ten
years,
which
used
metal-free
conditions
to
prepare
indoles
starting
from
alkynes
and
nitrogen
compounds.
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Авг. 8, 2024
Palladium
catalyzed
tandem
reaction
represents
a
one-pot
synthetic
approach
to
efficiently
synthesize
complex
functionalized
molecules
while
reducing
steps,
aligning
with
the
principles
of
green
chemistry.
However,
achieving
direct
cascade
aza-Wacker
and
Povarov
reactions
in
synthesis
presents
challenge
due
substrate
compatibility
issues
between
two
reactions.
In
this
work,
we
describe
an
aza-Wacker/Povarov
employing
highly
electrophilic
palladium
catalyst,
which
effectively
converts
anilines
1,6-dienes
into
hexahydro-cyclopenta[b]quinolines.
The
optimized
conditions
yield
up
79%,
diastereoselectivity
>
20:1.
Substrate
range
testing
reveals
various
sensitive
functional
groups,
successful
late-stage
modifications
are
performed
on
several
natural
products
drug
molecules,
demonstrating
versatility
practicality
method.
Additionally,
preliminary
investigation
mechanism
suggests
process
followed
by
process.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7551 - 7556
Опубликована: Май 15, 2023
Herein,
we
report
facile,
atom-economical
syntheses
of
multisubstituted
2,3-dihydropyrroles
using
flavin–iodine-catalyzed
aerobic
oxidative
multistep
transformations
chalcones
with
β-enamine
ketones
or
1,3-dicarbonyl
compounds
and
amines.
Exploiting
coupled
flavin–iodine
catalysis,
the
reaction,
including
C–C
C–N
bond
formation,
is
promoted
only
by
consumption
O2
(1
atm),
thus
allowing
synthesis
that
generates
green
H2O
as
waste.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(6), С. 4661 - 4670
Опубликована: Март 6, 2021
A
novel
visible
light
mediated
redox-neutral
1,3-dipolar
cycloaddition
of
2H-azirines
with
2,4,6-triarylpyrylium
tetrafluoroborate
salts
providing
tetrasubstituted
pyrroles
has
been
developed.
The
salt
acts
as
dipolarophile
well
photosensitizer
in
the
reaction,
under
blue
irradiation.
control
experiments
indicated
single
electron
oxidation
by
photoexcited
pyrylium
salts,
followed
coupling
between
an
azaallenyl
radical
cation
and
triarylpyranyl
key
mechanistic
feature.
mild
conditions,
wide
substrate
scope,
complete
regioselectivity
are
noticeable
attributes
reaction.
Chemical Communications,
Год журнала:
2023,
Номер
59(71), С. 10636 - 10639
Опубликована: Янв. 1, 2023
The
first
copper-catalyzed
three-component
annulation
of
α,β-unsaturated
ketoximes,
1,3-dicarbonyls
and
paraformaldehyde
has
been
documented.
This
novel
strategy
achieved
the
two
C-C
bond
cleavage
1,3-dicarbonyl
compounds
directly
as
a
single-carbon
synthon
provided
new
highly
efficient
method
for
synthesis
2,3-disubstituted
pyrroles
in
moderate
to
good
yields
with
broad
functional
group
compatibility.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(21), С. 15501 - 15506
Опубликована: Окт. 18, 2023
A
new
metal-free
method
for
the
rapid,
productive,
and
scalable
preparation
of
3-trifluoromethyl
pyrroles
has
been
developed.
It
is
based
on
electrophilic
nature
double
bond
β-CF3-1,3-enynamides
due
to
electron-withdrawing
characteristics
trifluoromethyl
groups
strong
nucleophilic
alkyl
primary
amines.
Evidence
highly
regioselective
1,4-hydroamination
was
observed
after
isolation
characterization
allenamide
intermediate.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(23), С. 4704 - 4719
Опубликована: Янв. 1, 2024
This
protocol
is
solvent
free,
requires
a
lower
amount
of
phosphine-free
highly
stable
catalyst,
produces
an
excellent
yield
with
green
by-product
only.
Besides,
it's
applicability
in
broad
substrate
scope
and
scalable
as
well.
