The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(12), P. 8017 - 8027
Published: June 6, 2022
A
base-mediated
annulation
of
2-nitrobenzothiophenes
with
naphthols
was
realized
for
the
synthesis
hitherto
unknown
class
heteroacenes,
namely
benzothieno[2,3-b]naphthofurans.
By
using
a
hydroxyl
group
positioned
at
1st
or
2nd
position,
we
could
synthesize
two
positional
isomers,
benzothieno[2,3-b]naphtho[2,1-d]furans
benzothieno[2,3-b]naphtho[2,3-d]furans.
The
found
to
be
general
range
substituted
and
naphthols.
This
heteroannulation
benzothiophene
extended
phenols
affording
corresponding
benzothieno[2,3-b]benzofurans
in
moderate
yields.
basic
photophysical
properties
these
heteroacenes
were
evaluated,
also
demonstrated
applicability
this
on
gram
scale.
Chemical Communications,
Journal Year:
2020,
Volume and Issue:
56(17), P. 2586 - 2589
Published: Jan. 1, 2020
An
efficient
enantioselective
dearomatization
of
2-nitrobenzofurans
was
realized
via
an
organocatalyzed
one-step
Michael
addition
process.
This
method
provides
a
facile
strategy
to
access
range
structurally
diverse
3,3'-disubstituted
oxindoles,
which
feature
intriguing
combination
two
privileged
motifs
including
3-pyrrolyl-substituted-oxindoles
and
2,3-dihydrobenzofurans
substructures,
in
excellent
results.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(18), P. 7088 - 7093
Published: Aug. 28, 2020
The
first
catalytic
enantioselective
dearomatization/rearomatization
of
2-nitroindoles
triggered
by
the
Michael
addition
3-monosubstituted
oxindoles
was
established.
A
wide
range
3-indolyl-3'-alkyloxindoles
(up
to
99%
yield,
97%
ee)
and
3-indolyl-3'-aryloxindoles
95%
were
obtained
using
an
organocatalyst.
This
method
provides
unprecedented
strategy
access
structurally
diverse
3,3'-disubstituted
bearing
a
sterically
congested
triaryl-containing
all-carbon
quaternary
stereocenter.
utility
this
approach
verified
formal
synthesis
cyclotryptamine
alkaloids.
Chemistry - A European Journal,
Journal Year:
2021,
Volume and Issue:
28(2)
Published: Oct. 29, 2021
The
application
of
dinuclear
zinc
catalysts
in
a
dearomatization
reaction
has
been
developed.
Catalytic
asymmetric
[3+2]
annulations
2-nitrobenzofurans
or
2-nitrobenzothiophenes
with
CF3
-containing
N-unprotected
isatin-derived
azomethine
ylides
catalyzed
by
are
realized
excellent
diastereomer
ratios
(dr)
>20
:
1
and
enantiomeric
excess
(ee)
up
to
99
%.
This
protocol
provides
practical,
straightforward
access
structurally
diverse
pyrrolidinyl
spirooxindoles
containing
2,3-fused-dihydrobenzofuran
(or
dihydrobenzothiphene)
moiety,
four
contiguous
stereocenters.
Reactions
can
be
performed
on
gram
scale.
absolute
configuration
products
is
confirmed
X-ray
single
crystal
structure
analysis,
possible
mechanism
proposed.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(5), P. 1814 - 1819
Published: Feb. 16, 2021
We
have
developed
a
metal-free,
mild,
and
green
synthetic
route
toward
benzothieno[3,2-b]benzofurans
by
the
annulation
of
3-nitrobenzothiophene
with
phenols.
The
reaction
was
found
to
be
general
range
substituted
In
addition,
we
could
extend
methodology
for
synthesis
pentacenes
demonstrate
in
gram-scale.
Moreover,
extended
strategy
benzothieno[2,3-b]benzofurans
starting
from
2-nitrobenzothiophenes.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(41), P. 22184 - 22188
Published: July 17, 2021
Abstract
Herein
we
report
a
Pd‐catalyzed
dearomative
methoxyallylation
of
3‐nitroindoles
with
readily
available
allyl
carbonates.
Good
yields
(up
to
86
%)
and
diastereoselectivity
>20:1
dr)
are
obtained
for
wide
range
substrates.
The
compatibility
gram‐scale
synthesis
the
relatively
low
catalyst
loading
(down
1
mol
%
[Pd])
enhance
practicality
this
method.
kinetic
experiments
indicate
that
rate‐determining
step
reaction
is
nucleophilic
attack
alkoxide
anion.
Asian Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
10(6), P. 1345 - 1376
Published: April 19, 2021
Abstract
Chiral
analogues
of
squaramides
have
been
fruitful
in
organocatalyzed
asymmetric
reactions
over
last
decade.
Alongside
other
H‐bonding
catalysts
like
ureas,
thioureas:
proved
to
be
efficient
for
the
formation
acyclic
and
cyclic
chiral
molecules.
A
wide
range
molecules
bearing
multiple
functionalities
stereocenters
synthesized
by
using
several
bifunctional
as
catalysts.
These
perform
base
utilizing
basic
N
atom
their
extension
help
stereoinduction
forming
H‐bonds
with
suitable
H‐bond
acceptors.
The
present
review
focuses
on
assembling
recent
progresses
synthesis
five
six
membered
rings
promoted
squaramides.
handful
articles
published
research
groups
documenting
construction
five‐
six‐membered
part
interesting
complex
molecular
architectures.
Different
methodologies
conventional
formal
cycloadditions
or
cascade
engineered
through
assistance
fabricate
carbo‐
heterocycles.
This
also
includes
dual
cooperative
catalytic
system
which
squaramide
is
one
European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
2022(18)
Published: April 5, 2022
Abstract
Dearomatization
reactions
employing
simple
aromatic
compounds
have
showcased
remarkable
progress
in
the
recent
decade
and
emerged
as
one
of
most
straightforward
powerful
tools
for
creation
highly
functionalized,
three‐dimensional
molecular
frameworks
commonly
encountered
medicinal
chemistry
life
sciences.
Among
use,
nitro(hetero)arenes,
which
feature
a
less
pronounced
character
due
to
presence
electron‐withdrawing
nitro
group,
been
extensively
used
different
types
dearomatization
reactions.
The
dearomative
annulation
reaction
serves
versatile
method
construction
complex
polycyclic
systems.
This
overview
presents
brief
summary
impressive
advances
nitro(hetero)arenes
provides
some
inspirations
future
research.
The Chemical Record,
Journal Year:
2023,
Volume and Issue:
23(7)
Published: Jan. 3, 2023
Abstract
The
sulfa‐Michael
addition
reaction
is
a
crucial
subset
of
the
Michael
reaction,
and
aroused
interest
numerous
synthetic
biologists
chemists.
In
particular,
triggered
cascade
has
developed
quickly
in
recent
years
because
it
offers
an
efficient
method
to
construct
C−S
bonds
other
one
approach,
which
widely
applicable
for
building
chiral
pharmaceuticals,
their
intermediates,
natural
compounds.
This
review
emphasizes
advancements
addition‐triggered
reactions
stereoselective
synthesis
sulfur‐containing
compounds,
including
sulfa‐Michael/aldol,
sulfa‐Michael/Henry,
sulfa‐Michael/Michael,
sulfa‐Michael/Mannich
some
multi‐step
processes.
Moreover,
mechanisms
derivatization
experiments
are
introduced
appropriately.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(15), P. 10427 - 10439
Published: July 27, 2021
The
first
application
of
3-alkyl-2-vinylindoles
in
catalytic
asymmetric
dearomative
cycloadditions
was
established
by
chiral
phosphoric
acid
(CPA)-catalyzed
(2+3)
cycloaddition
with
azoalkenes,
leading
to
the
generation
pyrroloindolines
bearing
two
tetrasubstituted
stereogenic
centers
good
yields
(61–96%)
and
excellent
stereoselectivities
(all
>95:5
dr,
86–99%
ee).
This
reaction
has
realized
enantioselective
3-alkyl-2-vinylindoles,
which
brings
a
new
reactivity
this
class
vinylindoles
will
enrich
chemistry
3-alkyl-2-vinylindoles.
In
addition,
approach
provided
useful
strategy
for
construction
enantioenriched
pyrroloindoline
skeletons
centers.
More
importantly,
bioassay
these
revealed
that
some
compounds
exhibit
strong
anti-cancer
activity
against
Hela
MCF-7
cell
lines,
be
helpful
discovering
drug
candidates.
