C3 versus C5 Regioselectivity in the Intramolecular Dehydrative Friedel–Crafts Alkylation of Indole C4-Tethered Carbinols
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 3, 2025
Described
herein
is
a
mild
catalytic
dehydrative
Friedel-Crafts
alkylation
of
1,1-diarylalkanols─a
challenging
reaction
with
exceedingly
rare
previous
success,
presumably
because
the
unfavorable
steric
hindrance
around
reactive
centers
and
competitive
E1
reaction.
Executing
in
an
intramolecular
fashion
benefiting
from
high
nucleophilicity
indole,
we
have
successfully
utilized
this
synthesizing
3,4-fused
indoles.
Interestingly,
strategy
could
also
be
applied
to
access
4,5-fused
indoles
via
modification
tether
connecting
alcohol
indole
moieties.
Язык: Английский
Dearomative Alkylation-Based Two-Step cis-Diastereoselective Synthesis of Indoline-2,3-Fused Chromans and Tetrahydropyrans
Raju Chouhan,
Nandini Ray,
Nitish Nayan Gogoi
и другие.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 3, 2024
Herein,
we
describe
a
two-step,
Язык: Английский
Switchable Skeletal Rearrangement of Hexahydro-4H-indol-4-ones: Divergent Synthesis of Dihydroxy-4H-cyclopenta[b]pyridin-4-ones and 8-Alkenyl Oxepane-2,6-diones
Organic Letters,
Год журнала:
2024,
Номер
26(20), С. 4205 - 4211
Опубликована: Май 14, 2024
An
unprecedented
base-controlled
selective
skeletal
rearrangement
reaction
of
hexahydro-4
Язык: Английский
A Catalytic Intramolecular Aldehyde–Alkyne Metathesis Approach to Azepino[1,2‐a]indoles
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(21), С. 4452 - 4461
Опубликована: Июль 23, 2024
Abstract
Reported
herein
is
a
method
for
the
construction
of
azepino[1,2‐
]indoles
via
an
intramolecular
aldehyde–alkyne
metathesis
1‐(5‐aryl‐4‐pentynyl)indole‐2‐carbaldehydes.
This
Sc(OTf)
3
‐catalyzed
reaction
has
several
remarkable
features,
such
as
ready
accessibility
starting
materials,
broad
substrate
scope,
operational
simplicity,
and
high
yields.
The
practicality
process
synthetic
potential
products
were
demonstrated
with
upscaling
experiment
downstream
derivatizations
obtained
products.
We
have
also
extended
this
methodology
to
synthesize
6,7‐dihydropyrido[1,2‐
]indole
derivative.
Язык: Английский
HFIP-Mediated Cascade Aminomethylation and Intramolecular Cyclization of Allenamides with N,O-Acetals to Access Tetrahydro-β-carboline Derivatives
Chemical Communications,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
cascade
of
two
C–C
bond
forming
reactions
promoted
alone
by
HFIP
is
described
delivering
tetrahydro-β-carboline
derivatives
embedded
with
an
allylic
amine
functionality.
Язык: Английский
Total Syntheses of Uvarindoles A and B, (±)-Pseudophrynaminol, and (±)-Pseudophrynamines 272A and 270 via Dearomative Indole Alkylation
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 31, 2025
Herein,
we
report
the
first
total
synthesis
of
alkaloid
uvarindole
B
with
an
overall
yield
49%
over
five
steps
via
double
C3-alkylation
5-bromoindole,
Plancher
rearrangement,
and
Negishi
coupling
as
key
steps.
We
also
disclose
short
syntheses
A,
pseudophrynaminol,
pseudophrynamines
272A
270
dearomative
indole
alkylation.
Язык: Английский
Interrupted Plancher Rearrangement Initiated by Dearomative Epoxide–Indole Cyclization: Formal Umpolung Reactivity of Indoles
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 12, 2024
We
herein
report
the
serendipitous
discovery
of
interrupted
Plancher
rearrangement
initiated
by
an
HFIP-promoted
dearomative
epoxide-indole
cyclization,
unlocking
a
new
blueprint
to
formal
C3
umpolung
reactivity
indoles.
This
rapid
complexity
generating
cascade
process
paves
way
toward
class
fused-bridged
indolines
in
high
yields
and
under
full
regio-
diastereocontrol.
The
reaction
is
amenable
wide
range
substituents
starting
materials.
Язык: Английский
Au(i)/Sc(iii)-co-catalyzed tandem spiroannulation/cycloisomerization of 3-(2-ethynylaryl)-N-tosylaziridines with indoles to access 5H-benzo[b]carbazoles
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(29), С. 5999 - 6003
Опубликована: Янв. 1, 2024
An
unusual
Au(
i
)/Sc(
iii
)-co-catalyzed
tandem
spiroannulation/cycloisomerization
of
3-(2-ethynylaryl)-
N
-tosylaziridine-2,2-diesters
with
indoles
has
been
reported.
A
variety
5
H
-benzo[
b
]carbazoles
were
obtained
in
moderate
to
good
yields
(30–88%).
Язык: Английский
Constructing spirooxindoles from non-oxindole precursors: a one-pot nitro-reduction/double lactamization approach to spiro[indoline-3,3'-quinoline]-2,2'-diones
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(37), С. 7601 - 7606
Опубликована: Янв. 1, 2024
2-(2-Nitrobenzyl)-2-(2-nitrophenyl)malonates,
readily
prepared
by
S
Язык: Английский