Stereoselective Palladium‐Catalyzed C(sp3)−H Mono‐Arylation of Piperidines and Tetrahydropyrans with a C(4) Directing Group
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(8), P. 1488 - 1497
Published: March 1, 2022
Abstract
A
selective
Pd‐catalyzed
C(3)−H
cis
‐functionalization
of
piperidine
and
tetrahydropyran
carboxylic
acids
is
achieved
using
a
C(4)
aminoquinoline
amide
auxiliary.
High
mono‐
‐selectivity
attained
by
mesityl
acid
as
an
additive.
Conditions
are
developed
with
significantly
lower
reaction
temperatures
(≤50
°C)
than
other
reported
heterocycle
C(
sp
3
)−H
functionalization
reactions,
which
facilitated
DoE
optimization.
one‐pot
C−H
functionalization‐epimerization
procedure
provides
the
trans
‐3,4‐disubstituted
isomers
directly.
Divergent
removal
accomplished
installation
acid,
alcohol,
nitrile
functional
groups.
Overall,
fragment
compounds
suitable
for
screening
generated
in
3–4
steps
from
readily‐available
heterocyclic
acids.
magnified
image
Language: Английский
Ru-Catalyzed One-Pot Synthesis of Heterocyclic Backbones
Catalysts,
Journal Year:
2023,
Volume and Issue:
13(1), P. 87 - 87
Published: Jan. 1, 2023
Ruthenium
complexes
are
remarkable
catalysts
for
the
C–H
activation
approaches
and
organic
transformations.
Combining
a
Ru-catalyst
with
oxidants
other
additives
in
one-pot
process
is
considered
sustainable
approach
due
to
reduction
reaction
steps
minimal
usage
of
solvents
during
synthesis,
work-up,
isolation
chemicals,
purification
products.
This
review
highlights
ruthenium-catalyzed
transformations
manner
achieve
heterocyclic
backbones,
including
indoles,
benzofurans,
indazoles,
pyrans,
pyrimidines,
quinolines,
isoquinolines.
Language: Английский
Rh-catalyzed cyclization of carbamates–synthesis of a new heterocyclic system: tetrahydro-3H-4-oxa-2-thia-2b-azacyclopropa[cd]pentalen-3-one 2,2-dioxide
Chemical Papers,
Journal Year:
2023,
Volume and Issue:
77(11), P. 7249 - 7254
Published: Aug. 10, 2023
Language: Английский
Construction of Benzo‐Fused Heterocycles by Epoxide–Heteronucleophile Cyclization: Applications in the Synthesis of Natural Products and Designed Molecules
European Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
2022(11)
Published: Oct. 20, 2021
Abstract
Construction
of
benzo‐fused
heterocycles,
specifically
which
have
one
or
more
sp
3
stereogenic
carbon
atoms
on
the
heterocyclic
ring,
by
intramolecular
ring‐opening
cyclization
epoxides
with
O
‐
and
N
‐nucleophiles
is
a
powerful
synthetic
tool
in
organic
synthesis.
In
this
Review,
we
analyze
efficiency
such
heterocyclization
approach
natural
product
synthesis
methodologies
published
since
year
2000.
addition
to
briefly
discussing
methods
accessing
requisite
epoxide
substrates,
important
aspects
subsequent
reaction,
as
reaction
conditions,
endo
versus
exo
‐regioselectivity,
protecting
functional
group
compatibility,
enantio‐
distereoselectivity
are
surveyed.
Although
literature
chemistry
last
four
decades
has
witnessed
large
number
reviews/book
chapters
chemistry,
title
topic
never
been
reviewed.
Herein,
systematized
it
dedicated
review
for
first
time.
Language: Английский
Synthesis of 2-hexyl-5-ethylfuran-3-sulfonic acid (HEFS) – natural antithrombosis agent from Eisenia earthworms
Chemistry of Heterocyclic Compounds,
Journal Year:
2023,
Volume and Issue:
59(6-7), P. 512 - 516
Published: July 1, 2023
Language: Английский
Rh-Catalyzed cyclization of carbamates – synthesis of a new heterocyclic system: tetrahydro-3H-4-oxa-2-thia-2b-azacyclopropa[cd]pentalen-3-one 2,2-dioxide
Research Square (Research Square),
Journal Year:
2023,
Volume and Issue:
unknown
Published: June 26, 2023
Abstract
A
simple
method
for
the
synthesis
of
five-
and
six-membered
ring
sulfone
carbamates
was
elaborated.
The
includes
reaction
corresponding
starting
alcohols
with
trichloroacetyl
isocyanate
following
hydrolysis
protecting
group
potassium
carbonate
in
methanol.
Rh
2
(OAc)
4
catalyzed
cyclization
investigated.
It
shown
that
saturated
moiety
tend
to
give
products
elimination
carbamic
acid
(corresponding
unsaturated
sulfones)
due
high
acidity
C-H
bond
α-position
ring.
Unsaturated
carbamate
(1,1-dioxido-2,3-dihydrothiophen-3-yl
carbamate)
similar
conditions
afforded
new
heterocyclic
system
confirmed
by
2D
NMR:
tetrahydro-3
H
-4-oxa-2-thia-2b-azacyclopropa[
cd
]pentalen-3-one
2,2-dioxide.
This
result
can
be
explained
more
favorable
aziridination
double
C=C
nitrenoid
intermediate
compared
pathway.
In
silico
pharmacological
profile
compound
evaluated.
showed
good
ADME
acute
toxicity
properties
probability
level
anticancer
activity
prostate
carcinoma
cell
line
PC-3.
Language: Английский