The Journal of Organic Chemistry,
Год журнала:
2020,
Номер
85(16), С. 10835 - 10845
Опубликована: Июль 21, 2020
A
Rh(III)-catalyzed
direct
cyanation
of
2H-indazoles
with
N-cyano-N-phenyl-p-toluenesulfonamide
has
been
realized
via
a
chelation-assisted
strategy.
The
methodology
enables
regioselective
access
to
various
ortho-cyanated
phenylindazoles
in
good
yields
broad
substrate
scope
and
functional
group
compatibility.
obtained
cyanated
indazoles
could
further
be
converted
into
other
value-added
chemicals.
Importantly,
the
current
protocol
is
featured
several
characteristics,
including
novel
cyanating
agent,
regioselectivity,
operational
convenience.
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
362(18), С. 3768 - 3794
Опубликована: Май 28, 2020
Abstract
Indazoles
are
a
very
important
class
of
N‐containing
heterocycles
with
wide
range
biological
and
medicinal
properties.
The
presence
different
functionalities
on
indazole
moieties
enhances
its
activities.
Hence,
the
preparation
compounds
bearing
functional
groups
has
gained
significant
interest
to
organic
synthetic
chemists.
A
large
effort
been
made
develop
efficient
new
methods
for
functionalization
indazoles.
Direct
catalytic
is
powerful
tool
facile
synthesis
derivatives
due
straightforwardness.
This
review
summarizes
developments
direct
functionalizations
indazoles
published
in
last
two
decades.
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Organic Chemistry Frontiers,
Год журнала:
2020,
Номер
7(12), С. 1527 - 1569
Опубликована: Янв. 1, 2020
Heterocyclic
alkenes
and
their
derivatives
are
an
important
class
of
reactive
feedstock
valuable
synthons.
This
review
highlights
the
transition-metal-catalyzed
coupling
heterocyclic
alkenesviaa
C–H
functionalization
strategy.
Organic Letters,
Год журнала:
2020,
Номер
22(14), С. 5605 - 5609
Опубликована: Июнь 24, 2020
A
general
and
practical
method
for
the
direct
C-H
amination
of
2H-indazoles
with
a
series
amines
including
aliphatic
primary
amines,
secondary
azoles,
sulfoximines
via
organophotoredox-catalyzed
oxidative
coupling
has
been
disclosed
at
room
temperature
under
ambient
air
conditions.
Additionally,
this
protocol
is
used
free
aminated
2H-indazole
synthesis.
mechanistic
study
revealed
that
single
electron
transfer
(SET)
pathway
might
be
involved
in
reaction.
Organic Letters,
Год журнала:
2022,
Номер
24(6), С. 1280 - 1285
Опубликована: Фев. 7, 2022
Synthesis
of
spiro[benzo[d][1,3]oxazine-4,4'-isoquinoline]s
through
a
unique
[4+1+1]
annulation
N-aryl
amidines
with
diazo
homophthalimides
and
O2
is
presented.
This
unprecedented
spirocyclization
reaction
features
readily
obtainable
substrates,
structurally
pharmaceutically
attractive
products,
cost-free
clean
oxygen
source,
sustainable
medium,
tolerance
broad
spectrum
functional
groups,
an
interesting
mechanism
based
on
sequential
C(sp2)-H/C(sp3)-H
bond
cleavage
insertion.
Organic Letters,
Год журнала:
2023,
Номер
25(24), С. 4422 - 4428
Опубликована: Июнь 8, 2023
Presented
herein
is
a
condition-controlled
selective
synthesis
of
pyranone-tethered
indazoles
or
carbazole
derivatives
via
the
cascade
reactions
N-nitrosoanilines
with
iodonium
ylides.
Mechanistically,
formation
former
involves
an
unprecedented
process
including
nitroso
group-directed
C(sp2)–H
bond
alkylation
N-nitrosoaniline
ylide
followed
by
intramolecular
C-nucleophilic
addition
to
moiety,
solvent-assisted
cyclohexanedione
ring
opening,
and
transesterification/annulation.
On
contrary,
latter
initial
annulation
denitrosation.
These
developed
protocols
feature
easily
controllable
selectivity,
mild
reaction
conditions,
clean
sustainable
oxidant
(air),
valuable
products
that
are
structurally
diverse.
In
addition,
utility
was
showcased
their
facile
diverse
transformations
into
synthetically
biologically
interesting
compounds.
Organic Letters,
Год журнала:
2023,
Номер
25(5), С. 720 - 725
Опубликована: Янв. 27, 2023
Presented
herein
is
a
solvent-dependent
selective
synthesis
of
CF3-tethered
indazole
derivatives
via
the
cascade
reactions
1-arylpyrazolidinones
with
trifluoromethyl
ynones.
Mechanistically,
formation
title
products
involves
N–H/C–H/C–N/C–C
bond
cleavage
along
pyrazole
ring
and
pyrazolidinone
opening.
For
scaffold,
1-phenylpyrazolidinone
acts
as
C2N2
synthon,
while
ynone
serves
C1
synthon.
Meanwhile,
also
an
enol
unit
to
facilitate
opening
provide
trifluoropropenoxy
fragment
alkynyl
triple
migration
cleaved
moiety.
When
reaction
was
run
in
trifluoroethanol
instead
DCE,
it
selectively
afforded
tethered
trifluoroethoxy
moiety
through
situ
transesterification.
To
our
knowledge,
this
first
concurrent
activation,
formation,
CF3
migration.
Chemical Science,
Год журнала:
2024,
Номер
15(30), С. 12042 - 12046
Опубликована: Янв. 1, 2024
Under
blue
light
vinyldiazoacetate
reagents
selectively
form
unstable
cyclopropenes
that
undergo
intermolecular
cycloaddition
reactions
at
a
faster
rate
than
their
competitive
ene
dimerization.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(13), С. 3238 - 3243
Опубликована: Янв. 1, 2021
Herein,
a
novel
synthesis
of
pyrazolidinone
fused
1,3-benzooxazepine
derivatives
via
formal
[4
+
3]
annulation
reaction
1-phenylpyrazolidinones
with
diazonaphthalen-2(1H)-ones
is
presented.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(14), С. 3600 - 3606
Опубликована: Июнь 10, 2021
Abstract
Presented
herein
is
a
selective
synthesis
of
3‐(α‐fluorovinyl)indoles
and
3‐acylindoles
via
the
coupling
1‐phenylpyrazolidinones
with
α,α‐difluoromethylene
alkynes.
Mechanistically,
formation
resulted
from
cascade
process
including
Rh(III)‐catalyzed
ortho
‐C−H
bond
cleavage,
regioselective
triple
insertion,
pyrazolidinone
ring‐opening,
indole
ring‐formation
HF
elimination.
Interestingly,
when
this
reaction
was
carried
out
in
CH
3
OH/H
2
O
instead
CN,
situ
formed
readily
undergo
hydration
to
afford
3‐acylindole
derivatives.
This
protocol
features
controllable
selectivity,
simultaneous
both
heterocyclic
scaffold
monofluoroalkenyl
moiety,
atom‐economy,
substrate
diversity,
good
functional
group
tolerance
redox‐neutral
conditions.
Anticancer
screening
selected
products
against
two
human
cancer
cell
lines
demonstrated
their
potential
as
lead
compounds
for
drug
development.
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