Synthesis of Cyclopenta[b]indoles via Rhodium‐Catalyzed Cascade Migration‐Annulation of 1‐Sulfonyl‐1,2,3‐triazoles and Indoles
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(10), С. 1623 - 1628
Опубликована: Май 5, 2023
Abstract
A
rhodium‐catalyzed
cascade
1,3‐sulfinate
migration,
intermolecular
[3+2]
annulation
of
1‐sulfonyl‐1,2,3‐triazoles
and
indoles
was
achieved.
The
one‐pot
protocol
provided
a
method
to
construct
cyclopenta[
b
]indoles
bearing
four
stereocenters
in
45%
99%
yields
with
1.6:1
>20:1
diastereoselectivities.
In
addition,
could
be
transformed
into
variety
functionalized
compounds,
demonstrating
the
synthetic
value
this
migration‐annulation
strategy
ring
system
synthesis.
magnified
image
Язык: Английский
Construction of cyclopenta[b]dihydronaphthofurans via TsOH-catalyzed consecutive biscyclization of dithioallylic alcohols and 1-styrylnaphthols
Chemical Communications,
Год журнала:
2023,
Номер
59(16), С. 2275 - 2278
Опубликована: Янв. 1, 2023
An
efficient
TsOH-catalyzed
consecutive
biscyclization
cascade
reaction
of
dithioallylic
alcohols
with
1-styrylnaphthols
is
demonstrated
for
the
concise
construction
pharmaceutically
important
cyclopenta[b]dihydrobenzofuran
scaffolds.
This
process
involved
an
acid-catalyzed
(3+2)
cycloaddition
followed
by
intramolecular
nucleophilic
addition,
providing
cyclopenta[b]dihydronaphthofurans
bearing
a
tetra-
or
fully
substituted
cyclopentane
core
in
good
yields
exclusive
diastereoselectivities
(>20
:
1
d.r.).
Язык: Английский
Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds
Organic Letters,
Год журнала:
2021,
Номер
23(17), С. 6872 - 6876
Опубликована: Авг. 25, 2021
An
efficient
asymmetric
tandem
reaction
of
o-alkynylbenzaldehydes,
amines,
and
diazo
compounds
catalyzed
by
chiral
silver
imidodiphosphate
has
been
established.
Chiral
1,2-dihydroisoquinoline
analogues
have
a
tertiary
stereocenter
at
the
C1
position,
substituents
C3
position
are
available
with
up
to
97%
yields
98%
ee.
These
products
can
be
elaborated
into
corresponding
β-aminophosphonates
or
PARP1-inhibitor
analogues.
Язык: Английский
Construction of diverse spirooxindoles via a domino reaction of arylamines, but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones
Lingyun Zhu,
Jing Sun,
Dan Liu
и другие.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(47), С. 9392 - 9397
Опубликована: Янв. 1, 2023
An
iodine-promoted
domino
reaction
of
arylamines/benzylamines,
dialkyl
but-2-ynedioates
and
3-hydroxy-3-(indol-3-yl)indolin-2-ones
showed
very
interesting
molecular
diversity.
The
in
acetonitrile
at
65
°C
the
presence
30%
mmol
I2
resulted
spiro[indoline-3,1'-pyrido[4,3-b]indoles]
satisfactory
yields.
When
anilines
without
para-substituents
were
used
reaction,
a
direct
substitution
hydroxyl
group
to
2-(phenylamino)maleate
para-position
aniline
gave
chain
products
good
Additionally,
similar
reactions
with
benzylamines
not
only
spiro[indoline-3,1'-pyrido[4,3-b]indoles],
but
also
afforded
spiro[indoline-3,1'-pyrano[4,3-b]indol]-2-ones
lower
A
plausible
annulation
mechanism
was
rationally
proposed
for
formation
different
kinds
polycyclic
compounds.
Язык: Английский
Lewis acid-catalyzed [3 + 2] annulations of oxindole based spirocyclic donor–acceptor cyclopropanes with ynamides
Organic & Biomolecular Chemistry,
Год журнала:
2021,
Номер
19(44), С. 9645 - 9648
Опубликована: Янв. 1, 2021
[3
+
2]
annulations
of
spirocyclopropyl
oxindoles
with
ynamides
to
offer
biologically
important
spirocyclopenteneoxindoles
in
high
yields
good
diastereoselectivities
were
developed.
Язык: Английский
Imidodiphosphoric Acids Catalysed Asymmetric Functionaliza‐tion with Thiols: Access to Oxindole Derived ɑ‐Chiral Thioethers
Xiangshuo Qin,
Guofeng Jiang,
Jigang Gao
и другие.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
364(1), С. 225 - 231
Опубликована: Ноя. 9, 2021
Abstract
Chiral
imidodiphosphoric
acid‐catalysed
asymmetric
functionalization
of
3‐hydroxy
bisindoles
was
established.
Sulfur‐containing
groups
could
be
successfully
introduced
into
isatin
frameworks
using
commercially
available
thiols.
The
transformation
compatible
with
substrates
bearing
distinct
substituents,
both
aromatic
and
aliphatic
thiols
were
amenable
to
afford
the
desired
products.
A
total
41
reactions
furnished
various
chiral
3‐thiooxindoles
in
23%–99%
yield,
72%–99%
enantioselectivity.
magnified
image
Язык: Английский
Asymmetric Synthesis of Spiro[3,2′-morpholine-oxindoles] Derivatives via the [5 + 1] Annulation Reaction
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(23), С. 16815 - 16823
Опубликована: Ноя. 11, 2021
An
efficacious
method
in
which
BINOL-type
chiral
imidodiphosphoric
acid
catalyzed
the
asymmetric
[5
+
1]
annulation
reaction
of
2-pyrrolylphenol
with
1-methylindoline-2,3-dione
was
established.
The
strategy
tolerated
a
broad
substrate
scope,
and
30
examples
were
obtained.
A
range
enantioenriched
spiro[3,2′-morpholine-oxindole]
derivatives
incorporate
tertiary
stereocenter,
moderate
to
excellent
yields
(up
96%)
enantioselectivities
99%)
under
mild
conditions,
delivered.
Язык: Английский