An Approach to Functionally Embellished o-Alkynylbenzoates or Furan-3(2H)-ones from Diynones and DMAD: Controlled Divergence and Product Selectivity
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(6), С. 3945 - 3953
Опубликована: Март 2, 2023
The
discovery
of
reaction
regime
controlled
product
diversification
in
a
one-pot
between
diynones
and
dimethyl-1,3-acetonedicarboxylate
(DMAD)
to
selectively
furnish
either
functionally
unique
pentasubstituted
o-alkynylbenzoates
or
fully
substituted
furan-3(2H)-ones
is
delineated.
potential
these
two
versatile
platforms
enter
new
utilitarian
chemical
space
has
also
been
explored.
Язык: Английский
Photocatalytic Denitrative Alkenylation of Nitroalkanes
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 25, 2024
Reductive
radical
generation
has
become
a
cornerstone
of
modern
photoredox
chemistry.
However,
the
synthesis
functionalized
precursors
remains
tedious
multistep
process.
In
this
study,
we
focus
on
potential
nitro
group
as
redox-active
functional
and
present
denitrative
alkenylation
nitroalkanes,
facilitated
by
photoreductive
alkyl
radicals
from
nitroalkanes.
By
taking
advantage
facile
α-functionalization
successfully
generate
various
radicals,
which
are
subsequently
used
in
reactions.
Язык: Английский
One-Flask, Telescoped Synthesis of Pyrano[3,2-b]indol-2-ones from O-Nitroynones and β-Ketoesters: Further Advancement to Functionalized Carbazoles
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 19, 2025
A
new
general
strategy
for
accessing
pyrano[3,2-b]indol-2-ones,
a
promising
fused
hybrid
heterocyclic
system,
has
been
devised
from
o-nitroynones
and
β-ketoesters
through
one-flask
cascade
process
involving
tandem
Michael
addition,
intramolecular
cyclization,
Cadogan-Sundberg
reductive
cyclization.
The
utility
of
this
approach
further
amplified
by
leveraging
the
cycloaddition
proclivity
α-pyrone
moiety
in
pyrano[3,2-b]indol-2-ones
toward
concise
entry
to
carbazoles.
Illustrative
synthesis
carbazole
natural
products
hyellazole
chlorohyellazole
is
also
disclosed.
Язык: Английский
Enantioselective Michael addition of malonates to β,γ-unsaturated α-ketoesters catalysed by Cu(ii) complexes bearing binaphthyl–proline hybrid ligands
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(8), С. 1764 - 1770
Опубликована: Янв. 1, 2023
High
yields
(up
to
96%)
and
high
ee
92%)
were
achieved
for
chiral
copper(II)
complex-catalysed
enantioselective
Michael
addition
of
malonates
β,γ-unsaturated-α-ketoesters.
The
ligands
took
advantage
both
the
binaphthyl
proline
moieties,
substituents
with
different
electronic
steric
features
could
be
tolerated.
reactions
carried
out
under
mild
conditions,
a
gram
scale
reaction
realised
without
loss
yield
enantioselectivity.
Язык: Английский
Indeno-Annulation of o-Formyl-Ynones, o-Bis-Ynones, and p-Bis-o-Formyl-Ynones with Dimethyl Acetone-1,3-Dicarboxylate: One Flask Cascade Synthesis of Functionally Endowed 9-Fluorenols and Indeno[1,2-b]fluorenols
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(16), С. 11637 - 11649
Опубликована: Авг. 9, 2023
A
mild,
scalable,
one-pot
access
to
multifunctional
9-fluorenols
from
o-formyl-ynones
and
o-bis-ynones
on
reaction
with
dimethylacetone-1,3-dicarboxyate
through
tandem
Michael
addition-Aldol
condensation
cascade
has
been
conceptualized
executed.
The
scope
utility
of
this
synthetic
approach
have
further
amplified
for
entry
into
functionally
enhanced,
higher
order
fluorenols
like
pentacyclic
indeno[1,2-b]fluorene-6,12-diols
indeno[1,2-b]fluorene-6,12-diones
the
implementation
"double
indeno-annulation"
tactic
p-bis-o-formyl
ynones
dimethylacetone-1,3-dicarboxylate.
Besides
several
green
attributes,
current
is
also
compatible
emerging
time
energy
economy
features
a
swift
gateway
build
complexity.
Язык: Английский
Theoretical Investigation on Indeno-Annulation of O-Formyl-Ynone and P-Bis-O-Formyl-Ynone with Dimethylacetone-1,3-Dicarboxyate for Synthesis of 9‑Fluorenol and Indeno[1,2‑B]Fluorenol
Опубликована: Янв. 1, 2023
The
mechanism
is
investigated
for
indeno-annulation
of
o-formyl-ynone,
p-bis-o-formyl-ynone
with
DMAD
under
metal-free.
cascade
process
consists
Michael
addition,
aldol
reaction
condensation/aromatization.
addition
initiated
by
enol
form
via
nucleophilic
attack
to
ynone
delivering
accumulated
diene
the
first
new
C−C
bond.
From
ketone
isomer,
reaction/H
transfer
proceeds
producing
second
bond
and
five-membered
ring.
enol-ketone
tautomerism
annulation
are
prior
condensation
affording
third
another
six-membered
fluorenol
product
given
aromatization.
positive
solvation
effect
DMSO
solution
lies
in
reduction
absolute
activation
energies
reaction.
exerts
more
favorable
influence
on
simple
CHO
at
ortho-position
than
case
substituted
this
indeno-annulation.
These
results
supported
Multiwfn
analysis
FMO
specific
TSs
MBO
value
vital
bonding,
breaking.
Язык: Английский
Theoretical Investigation on Indeno-annulation of o-formyl-ynone and p-bis-o-formyl-ynone with Dimethylacetone-1,3-dicarboxyate for Synthesis of 9-fluorenol and Indeno[1,2-b]fluorenol
Acta Scientific Pharmaceutical Sciences,
Год журнала:
2024,
Номер
unknown, С. 03 - 13
Опубликована: Фев. 1, 2024
The
mechanism
is
investigated
for
indeno-annulation
of
o-formyl-ynone,
p-bis-o-formyl-ynone
with
DMAD
under
metal-free.The
cascade
process
consists
Michael
addition,
aldol
reaction
condensation/aromatization.Michael
addition
initiated
by
enol
form
via
nucleophilic
attack
to
ynone
delivering
accumulated
diene
the
first
new
C-C
bond.From
ketone
isomer,
reaction/H
transfer
proceeds
producing
second
bond
and
five-membered
ring.The
enol-ketone
tautomerism
annulation
are
prior
condensation
affording
third
another
six-membered
fluorenol
product
given
aromatization.The
positive
solvation
effect
DMSO
solution
lies
in
reduction
absolute
activation
energies
reaction.DMSO
exerts
more
favorable
influence
on
simple
CHO
at
ortho-position
than
case
substituted
this
indeno-annulation.These
results
supported
Multiwfn
analysis
FMO
specific
TSs
MBO
value
vital
bonding,
breaking.As
a
prime
objective
chemical
industry,
development
synthetic
methodologies
not
only
essential
sustainable
production
chemicals
but
also
related
efficiency,
step,
cost
environmental
impact
minimize
waste
ecological
footprint
[1-3].In
pursuit
goal,
catalysis
discipline
offering
efficient
versatile
strategies
sustainability
especially
formation
multiple
bonds
presenting
productive
direction.It
enables
expansion
enrichment
domino
or
tandem
processes
executed
one
flask
one-pot
fashion
thus
minimizing
number
purification
separation
steps
[4-6].The
construction
various
polycyclic
scaffolds
such
tactics
provides
privileged
category
expeditious
delivery
functional
complex
potential
drug
conjugates
involving
wide
range
pharmacological
activities
[7-9].In
field,
ynones
regarded
as
promising
platforms
many
reactive
sites
build
[10].The
reactions
variety
multifunctional
partner
often
unraveled
space.A
was
achieved
Ru-catalyzed
oxidative
alkynylation
oxetanols,
azetidinols
bicyclopentanols
ynones,
which
subsequently
converted
azetidine-,
oxetaneand
bicyclopentane-bearing
isoxazoles,
pyrazoles
pyrimidines
[11].Conjugated
alkynones
occupied
firm
position
among
building
blocks.The
base-catalyzed
substrate-controlled
dimerizations
aliphatic
were
focused
density
theory
(DFT)
study
understand
origin
selectivity
assembly
[12].The
cyclization
diazo
compounds
promoted
DBU
has
been
developed
synthesis
fused
eight-membered
oxocino[2,3-c]
single
step
highly
regio-and
diastereoselective
manner
[13].
Язык: Английский
Photocatalytic Denitrative Alkenylation of Nitroalkanes
Опубликована: Авг. 30, 2024
Reductive
radical
generation
has
become
a
cornerstone
of
modern
photoredox
chemistry.
However,
the
synthesis
functionalized
precursors
remains
tedious
multi-step
process.
In
this
study,
we
focus
on
potential
nitro
group
as
redox-active
functional
and
present
denitrative
alkenylation
nitroalkanes,
facilitated
by
photoreductive
alkyl
radicals
from
nitroalkanes.
By
taking
advantage
facile
α-functionalization
successfully
generate
various
radicals,
which
are
subsequently
used
in
reactions.
Язык: Английский
Reductive Homologation of Nitroalkanes via Denitrative Aminoalkylation
Organic Letters,
Год журнала:
2024,
Номер
26(42), С. 9046 - 9050
Опубликована: Окт. 16, 2024
We
present
the
reductive
homologation
of
nitroalkanes
through
utilization
denitrative
aminoalkylation
reaction.
This
transformation
is
accomplished
by
radical-radical
coupling
alkyl
radicals
derived
from
and
persistent
aminoalkyl
radicals.
By
capitalizing
on
diverse
α-functionalization
nitroalkanes,
α,β-multifunctionalized
amines
can
be
readily
accessed.
Язык: Английский
One flask cascade approach to complex pyrano[2,3-c]pyrazole-pyrazolone hybrid heterocyclic system and its initiatory neurobiological profiling
Chemical Communications,
Год журнала:
2024,
Номер
60(64), С. 8443 - 8446
Опубликована: Янв. 1, 2024
A
one-pot
multicomponent
approach
towards
a
hybrid
heterocyclic
pyrano[2,3-
Язык: Английский