NHC-Catalyzed Formal [4 + 2] Annulation of o-Formyl-Tethered Michael Acceptors and Ynones to Access Highly Functionalized Naphthalene Derivatives
Organic Letters,
Год журнала:
2024,
Номер
26(9), С. 1780 - 1786
Опубликована: Фев. 27, 2024
Herein
we
demonstrate
a
novel
organocatalytic
method
to
access
multifunctionalized
naphthalenes
via
an
NHC-catalyzed
reaction
of
ynones
and
o-formyl-tethered
Michael
acceptors.
The
presented
proceeds
through
intermolecular
Stetter
reaction–cyclization–aromatization
cascade
represents
rare
example
benzannulation
for
the
synthesis
substituted
arenes
by
using
ynone
as
two-carbon
synthon.
current
has
broad
substrate
scope;
postsynthetic
transformations
gram-scale
syntheses
highlight
practicality
displayed
methodology.
Язык: Английский
Base-Promoted Decarboxylative Annulation of Methyl 2-(2-Bromophenyl)acetates and Ynones to Access Benzoxepines
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(5), С. 3079 - 3088
Опубликована: Фев. 17, 2023
A
simple
and
efficient
base-mediated
decarboxylative
annulation
of
ynones
with
methyl
2-(2-bromophenyl)acetates
has
been
developed.
broad
range
benzoxepines
were
prepared
a
substrate
scope
high
regioselectivity
in
moderate
to
excellent
yields
under
transition-metal-free
conditions.
This
method
proceeds
through
tandem
[2
+
4]
annulation,
ring-opening
reaction,
the
intramolecular
nucleophilic
aromatic
substitution
reaction.
Additionally,
key
intermediates
successfully
obtained
characterized
unambiguously
by
single-crystal
X-ray
crystallography,
which
could
favorably
support
mechanism.
Furthermore,
gram-scale
reaction
synthetic
applications
for
further
functionalization
are
also
studied.
Язык: Английский
Ag(I)-Mediated Annulation of 2-(2-Enynyl)pyridines and Propargyl Amines to Access 1-(2H-Pyrrol-3-yl)indolizines
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(1), С. 304 - 312
Опубликована: Дек. 21, 2023
An
effective
Ag(I)-mediated
annulation
of
2-(2-enynyl)pyridines
and
propargyl
amines
was
developed,
unexpectedly
affording
a
broad
range
functionalized
1-(2H-pyrrol-3-yl)indolizines
in
moderate
to
excellent
yields.
The
developed
method
is
characterized
by
operational
simplicity,
ready
availability
starting
materials,
high
regioselectivity,
substrate
scope
under
mild
reaction
conditions.
Ag(I)-promoted
cyclization
possibly
results
the
formation
spiroindolizine,
ring-opening
rearrangement
which
may
give
1-(2H-pyrrol-3-yl)indolizine.
Furthermore,
gram-scale
synthetic
transformations
are
also
studied.
Язык: Английский
Transition-Metal-Free Synthesis of 3-Acyl Chromones by the Tandem Reaction of Ynones and Methyl Salicylates
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(21), С. 14005 - 14015
Опубликована: Окт. 10, 2022
A
facile
and
effective
tandem
reaction
of
ynones
methyl
salicylates
was
developed
to
obtain
a
broad
range
3-acyl
chromones
in
moderate-to-excellent
yields.
This
protocol
underwent
Michael
addition
cyclization
process,
which
exhibited
easily
accessible
substrates,
substrate
scope,
high
regioselectivity
under
mild
transition-metal-free
conditions.
Moreover,
gram-scale
further
chemical
transformation
the
products
were
also
studied.
Язык: Английский
A deconstruction–reconstruction strategy to access 1-naphthol derivatives: application to the synthesis of aristolactam scaffolds
Jeong Min Bak,
Moonyeong Song,
Inji Shin
и другие.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(44), С. 8936 - 8941
Опубликована: Янв. 1, 2023
A
deconstruction-reconstruction
strategy
for
the
synthesis
of
multisubstituted
polycyclic
aromatic
hydrocarbons
(PAHs)
is
delineated
herein.
The
deconstruction
step
enables
o-cyanomethylaroyl
fluorides
that
are
bifunctional
substrates
holding
both
a
pro-nucleophile
and
an
electrophile.
construction
involves
formal
[4
+
2]
benzannulation
using
active
methylenes.
utility
this
synthetic
method
also
demonstrated
by
tetracyclic
aristolactam
derivative.
Язык: Английский
Silver(I)-Promoted [3 + 3]-Cycloaddition of 2-(2-Enynyl)quinolines with N′-(2-Alkynylbenzylidene)hydrazides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(16), С. 11567 - 11575
Опубликована: Авг. 1, 2024
An
effective
and
straightforward
Ag(I)-mediated
annulation
of
2-(2-enynyl)quinolines
N'-(2-alkynylbenzylidene)hydrazides
was
developed,
forging
various
synthetically
challenging
17bH-isoquinolino[2'',1'':1′,6']pyridazino[4′,5′:3,4]pyrrolo[1,2-a]quinolines,
including
different
nitrogen-containing
fused
rings,
in
moderate
to
excellent
yields.
This
one-pot
cycloaddition
strategy
features
exclusive
regioselectivity,
high
atom
economy,
broad
substrate
scope
under
mild
conditions.
The
practicality
reliability
this
reaction
demonstrated
by
a
successful
scale-up
synthesis.
Язык: Английский
Base‐Catalyzed [4+2] Annulation of Ynones and Acetates for the Synthesis of 2‐Pyrones
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 30, 2024
Abstract
An
efficient,
practical,
and
scalable
Cs
2
CO
3
‐catalyzed
[4+2]
annulation
reaction
between
ynones
acetates
is
presented,
wherein
serve
as
the
four‐atom
partners.
This
methodology
facilitates
synthesis
of
substituted
2‐pyrones
with
yields
ranging
from
good
to
excellent.
The
ready
availability
starting
materials,
coupled
simplicity
protocol,
renders
this
approach
highly
amenable
preparation
a
diverse
range
2‐pyrones.
Furthermore,
feasibility
on
gram
scale
its
application
in
potent
selective
cyclooxygenase‐2
inhibitor
underscore
practical
significance
utility
method.
Язык: Английский