The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(13), С. 8562 - 8575
Опубликована: Июнь 14, 2022
A
novel
protocol
has
been
developed
for
the
preparation
of
highly
functionalized
2-azabicyclo[3.3.1]nonane
(morphan)
derivatives
by
interesting
three-component
cascade
reaction
3-formylchromones,
2-naphthol,
and
heterocyclic
ketal
aminals
(HKAs)
in
ionic
liquid
[BMIM]PF6
promoted
organic
base
Et3N.
complex
is
required,
which
includes
a
1,2-addition,
two
Michael
reactions,
tautomerizations,
an
N-alkylation
accompanied
ring-opening
involving
cleavage
one
C-O
bond
formation
four
bonds
(one
C-N
bond,
C-C
bonds).
As
result,
morphans
(5
6)
bearing
naphthalene-structured
skeletons
were
prepared
simple
heating
mixture
2-naphthols,
HKAs
environmentally
friendly
[BMIM]PF6.
This
can
be
used
synthesis
various
suitable
combinatorial
parallel
syntheses
natural-like
morphan
derivatives.
approach
several
advantages
such
as
use
solvent,
practical
operation
(multicomponent
one-pot
reaction),
satisfactory
yields
(65-88%).
Asian Journal of Organic Chemistry,
Год журнала:
2021,
Номер
10(12), С. 3101 - 3126
Опубликована: Окт. 22, 2021
Abstract
One‐pot
multi‐component
reactions
especially
under
transition‐metal‐free
catalysis
served
as
an
efficient,
and
environmentally
friendly
method
for
the
construction
of
value‐added
compounds.
Their
importance
in
organic
synthesis
has
drastically
increased
due
to
their
operational
simplicity,
cost‐effectiveness,
step‐
pot‐economic
nature.
On
other
hand,
molecular
hybridization
concept
recently
emerged
a
key
fascinating
area
medicinal
chemistry
design
new
drugs.
Owing
widespread
occurrence
natural
products,
pharmaceutical
agents,
incorporation
another
heterocycle
either
substituents
or
fused
material
into
4‐hydroxycoumarin
moiety
offers
opportunities
broad
application
targeted
coumarin‐heterocycles
many
branches
chemistry.
Considering
both
topics,
here
we
have
reviewed
developments
achieved
diverse
medicinally
privileged
oxygen,
nitrogen‐containing
heterocycles
well
spiro‐heterocycles
linked
with
coumarin
by
using
readily
accessible
starting
via
one‐pot
reaction
conditions.
Green Synthesis and Catalysis,
Год журнала:
2021,
Номер
3(1), С. 59 - 68
Опубликована: Окт. 25, 2021
A
novel
protocol
was
developed
for
the
construction
of
highly
functionalized
2-(diarylphosphoryl)-1,2-dihydropyridine
derivatives
(DAPDHPs)
from
3-formylchromones
(1),
heterocyclic
ketene
aminals
(HKAs,
2),
and
phosphine
oxides
(R2P(O)H,
3)
via
a
novel,
one-pot
cascade
reaction.
Optimization
reaction
conditions
determined
that
refluxing
mixture
3-formylchromones,
HKAs,
various
R2P(O)H
in
propylene
carbonate
(PC)
presence
triethylamine
as
base
facilitated
highest
yields
DAPDHP
products.
This
reaction,
which
involved
cleavage
one
C–O
bond
3-formylchromone
substrates
formation
three
new
bonds
(one
C–C,
C–N,
C–P
bond),
enabled
synthesis
small
library
The
dearomatized
products
were
formed
by
regioselective
nucleophilic
addition
reagents
to
intermediate
pyridinium
salts
8.
approach
has
several
advantages
such
use
an
environmentally-friendly
solvent,
simple
practical
operation
(with
filtration
washing
without
column
chromatography
separation),
good
yields,
product
with
potential
biological
activity.
Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(9)
Опубликована: Июль 29, 2023
Abstract
Multicomponent
reactions
(MCRs)
have
emerged
as
powerful
tools
in
synthetic
chemistry
for
the
efficient
synthesis
of
diverse
molecular
scaffolds,
particularly
nitrogen‐containing
heterocycles.
Despite
their
numerous
advantages,
use
transition
metal
catalysts
or
additives
MCRs
can
present
limitations
due
to
cost,
toxicity,
and
environmental
concerns.
In
recent
years,
there
has
been
a
growing
interest
metal‐free
N
‐heterocyclic
compounds.
This
review
provides
comprehensive
concise
overview
advancements
valuable
‐heterocycles
over
past
five
years.
The
is
systematically
organized,
categorizing
discussed
based
on
size
heterocyclic
ring
number
nitrogen
atoms.
Only
that
result
formation
rings
containing
at
least
one
atom
are
included,
while
derivatization
using
falls
outside
scope
this
review.
By
highlighting
developments
field,
aims
showcase
potential
significance
sustainable
strategies
accessing
elimination
metals
not
only
simplifies
reaction
conditions
but
also
contributes
greener
more
environmentally
friendly
approaches.
serves
resource
researchers
interested
design
application
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 11, 2025
A
new
approach
to
multifunctionalized
pyrroles
has
been
explored
by
the
tandem
cyclization
of
α-oxoketene-N,S-acetals
with
β-ketodinitriles
using
Cu(MeCN)4BF4
and
Ag2CO3
in
toluene
under
reflux
conditions.
The
reaction
involves
C–C/C–N
bond
creation,
is
assumed
proceed
via
enamine
formation,
intramolecular
cyclization,
rearrangement.
potential
methodology
also
demonstrated
for
a
gram-scale
as
well
some
useful
organic
transformations.
offers
practical
pathway
achieve
polysubstituted
broad
substrate
scope
good
functional
group
tolerance.
RSC Advances,
Год журнала:
2025,
Номер
15(13), С. 9676 - 9755
Опубликована: Янв. 1, 2025
The
tremendous
potential
of
transition
metal-free
multi-component
reactions
(MCR)
in
the
synthesis
N-heterocyclic
frameworks
is
examined
this
review,
offering
a
complete
overview
subject
matter.
discussion
on
mechanistic
rationale
reaction
routes
and
intermediates
provides
profound
insights
into
underlying
changes,
encouraging
deeper
investigation
various
molecular
frameworks.
This
review
serves
as
doorway
to
study
practicality
exploiting
these
for
efficient
uncomplicated
specific
nitrogen
heterocycles.
Specifically,
we
reveal
catalysts
field.
Because
their
extensive
scope
diversity,
enable
heterocycles
that
contain
nitrogen,
which
include
5-membered
(carbazole,
pyrimidines,
pyrroles)
6-membered
rings
(piperidine,
pyridine,
quinoline,
diazinane,
pyrazine,
quinoxaline,
1,2,3-triazine).
In
addition,
compatibility
with
functional
groups
substrates
not
only
increases
synthetic
value
compounds
but
also
broadens
relevance
domains
medical
chemistry,
materials
science,
other
relevant
areas
study.
To
motivate
future
development
field,
successful
examples
described
highlight
powerful
instruments
quick
general,
thorough
insightful
examination
catalysts,
highlighting
contemporary
organic
revolutionize
field
heterocycle
synthesis.
Chemical Communications,
Год журнала:
2023,
Номер
59(9), С. 1217 - 1220
Опубликована: Янв. 1, 2023
A
novel
protocol
for
the
synthesis
of
highly
functionalized
benzo[b][1,5]diazocin-6(5H)-one
derivatives
(BDCOs,
4
and
5)
from
2-aryl-1H-indoles
1,1-enediamines
was
developed
via
a
complex
cascade
reactions
including
regioselective
free
radical
oxidation,
1,2-addition
imine,
imine-enamine
tautomerization,
intramolecular
cyclization,
ring
expansion.
The
reaction
enabled
by
refluxing
mixture
two
substrates
in
presence
di-tert-butyl
peroxide
(DTBP)
as
an
oxidant
anhydrous
CuI
catalyst
toluene
under
argon
protection.
Consequently,
series
BDCOs
(4
were
synthesized
with
high
regioselectivity
good
yield.
This
can
be
used
one-pot
oxidative
annulation
rather
than
multi-step
reaction,
which
is
suitable
both
combinatorial
parallel
syntheses
BDCOs.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(18), С. 12482 - 12490
Опубликована: Сен. 2, 2022
A
new
metal-free
synthesis
of
pyrrole
from
allyl
ketone
and
amine
has
been
established.
The
reaction
proceeds
via
an
thiolative
activation
the
C–C
double
bond
with
dimethyl(methylthio)sulfonium
trifluoromethanesulfonate,
followed
by
a
nucleophilic
ring-opening
addition
primary
to
generated
episulfonium
intermediate,
then
internal
condensation
aromatization.
This
mild
procedure
provides
novel
strategy
construction
substituted
pyrroles
through
formal
[4
+
1]
cycloaddition
reaction.
