Ir(III)-Catalyzed Dual C–H Activation of 2-Aryl Phthalazinediones and 3-Aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides for the Construction of Spiro-Fused Cyclic Frameworks
Devulapally Yogananda Chary,
Minpoor Soumya Reddy,
Chidrawar Ajay
и другие.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(5), С. 2758 - 2772
Опубликована: Фев. 21, 2023
An
Ir(III)-catalyzed
double
C–H
activation
strategy
has
been
developed
for
the
synthesis
of
highly
rigid
spiro
frameworks
by
means
ortho-functionalization
2-aryl
phthalazinediones
and
2,3-diphenylcycloprop-2-en-1-ones
using
Ir(III)/AgSbF6
catalytic
system.
Similarly,
3-aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides
undergo
smooth
cyclization
with
to
afford
a
diverse
range
compounds
in
good
yields
excellent
selectivity.
Additionally,
2-arylindazoles
provide
corresponding
chalcone
derivatives
under
similar
reaction
conditions.
Язык: Английский
Rh(III)-Catalyzed Switchable [4 + 1] and [4 + 2] Annulation of N-Aryl Pyrazolones with Maleimides: An Access to Spiro Pyrazolo[1,2-a]indazole-pyrrolidine and Fused Pyrazolopyrrolo Cinnolines
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(6), С. 3424 - 3435
Опубликована: Март 3, 2023
A
rhodium(III)-catalyzed
controllable
[4
+
1]
and
2]
annulation
of
N-aryl
pyrazolones
with
maleimides
as
C1
C2
synthon
has
been
explored
for
the
synthesis
spiro[pyrazolo[1,2-a]indazole-pyrrolidines]
fused
pyrazolopyrrolo
cinnolines.
The
product
selectivity
was
achieved
through
time-dependent
annulation.
reaction
involves
sequential
Rh(III)-catalyzed
C-H
alkenylation
pyrazolone,
followed
by
an
intramolecular
spirocyclization
via
aza-Michael-type
addition
to
afford
spiro[pyrazolo[1,2-a]indazole-pyrrolidine].
However,
prolonged
time
converts
in
situ
formed
spiro[pyrazolo[1,2-a]indazole-pyrrolidine]
into
pyrazolopyrrolocinnoline.
This
unique
formation
switch
proceeds
strain-driven
ring
expansion
a
1,2-shift
C-C
bond.
Язык: Английский
Rh(III)‐Catalyzed C−H Activation/O‐Annulation for Construction of Divergent Spirosuccinimide and Maleimide‐Fused Isochromenes
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(22), С. 3915 - 3926
Опубликована: Сен. 12, 2023
Abstract
A
rhodium‐catalyzed
[5+1]
cycloaddition
via
C−H
activation/
O
‐annulation
strategy
for
synthesizing
biologically
interesting
isochromenes
is
presented.
This
protocol
selectively
provides
divergently
functionalized
containing
spirosuccinimide
and
maleimide
scaffolds
according
to
the
maleimides
itaconimides
used
as
substrates.
methodology
exhibits
an
extensive
substrate
scope,
remarkable
functional
group
tolerance,
high
regioselectivity.
Язык: Английский
Ruthenium-catalyzed (spiro)annulation of N-aryl-2,3-dihydrophthalazine-1,4-diones with quinones to access pentacyclic spiro-indazolones and fused-cinnolines
Sushma Naharwal,
Pidiyara Karishma,
Chikkagundagal K. Mahesha
и другие.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(23), С. 4753 - 4764
Опубликована: Янв. 1, 2022
Ru(II)-catalyzed
strategies
were
developed
for
the
[4
+
1]
and
2]
oxidative
coupling
between
N-aryl-2,3-dihydrophthalazine-1,4-diones
1,4-benzoquinones,
achieving
spiro-indazolones
fused-cinnolines,
respectively.
Mild,
aerobic
external
oxidant-free
conditions,
as
well
use
of
a
ruthenium
catalyst
such
(spiro)annulative
with
quinones
over
reported
Rh/Ir-catalyts,
underline
rewards
disclosed
protocols.
Язык: Английский
Rhodium(iii)-catalysed redox neutral alkylation of 3-arylbenzo[d]isoxazoles: easy access to substituted succinimides
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(29), С. 5985 - 5989
Опубликована: Янв. 1, 2023
A
convenient
method
for
the
alkylation
of
3-arylbenzo[d]isoxazoles
with
maleimides
under
redox-neutral
conditions
has
been
developed,
giving
a
series
substituted
succinimides
in
up
to
99%
yield.
This
transformation
is
highly
selective
give
succinimides,
and
Heck-type
products
are
successfully
avoided.
protocol
features
100%
atom-economy
broad
substrate
tolerance,
provides
novel
strategy
synthesis
diverse
an
opportunity
succinylation
protein
medication
pharmacologists
discover
first-in-class
drugs.
Язык: Английский
Rhodium‐Catalyzed Functionalization and Annulation of N‐Aryl phthalazinediones with Allyl Alcohols
Sushma Naharwal,
Narendra Dinkar Kharat,
Kiran Bajaj
и другие.
Chemistry - An Asian Journal,
Год журнала:
2024,
Номер
19(23)
Опубликована: Авг. 23, 2024
A
direct
ortho-Csp
Язык: Английский
Efficient synthesis of spirooxazine-pyrans via rhodium-catalyzed [3+3] cascade spiroannulation of benzoxazines with 1-diazonaphthalen-2(1H)-ones
Junwei Huang,
Xuelin Yue,
Yijie Gao
и другие.
New Journal of Chemistry,
Год журнала:
2023,
Номер
47(30), С. 14430 - 14435
Опубликована: Янв. 1, 2023
A
redox-neutral
access
to
spirooxazine-pyrans
has
been
realized
via
Rh(
iii
)-catalysed
[3+3]
cascade
spirocyclization
of
benzo[
b
][1,4]oxazines
and
1-diazonaphthalen-2(1
H
)-ones
under
extremely
mild
reaction
conditions.
Язык: Английский
Recent Progress in Transition Metal-Catalyzed C—H Bond Activation of N-Aryl Phthalazinones
Chinese Journal of Organic Chemistry,
Год журнала:
2022,
Номер
42(9), С. 2682 - 2682
Опубликована: Янв. 1, 2022
Язык: Английский
Rh(III)-catalyzed [5+1] spirocyclization to produce novel benzimidazole-incorporated spirosuccinimides
Green Synthesis and Catalysis,
Год журнала:
2022,
Номер
4(4), С. 338 - 341
Опубликована: Сен. 29, 2022
Transition-metal-catalyzed
cross-coupling
reactions
as
very
efficient
and
atom-economical
approaches
have
been
widely
used
to
build
up
complex
heterocyclic
compounds.
However,
modification
of
2-oxyl
benzimidazole
skeleton
using
maleimide
compounds
via
C–H
activation
has
remained
unprecedented.
Herein,
we
developed
a
rhodium(III)-catalyzed
[5
+
1]
cascade
spiroannulation
construct
diversified
novel
benzimidazole-incorporated
spirosuccinimide
derivatives
from
benzimidazoles
maleimides.
Язык: Английский