Synthesis,
Journal Year:
2023,
Volume and Issue:
55(24), P. 4181 - 4190
Published: Aug. 31, 2023
Abstract
We
report
a
practical
method
for
the
first
stereoselective
synthesis
of
diethyl
cis-
and
trans-(4-hydroxy-1,2,3,4-tetrahydroquinolin-2-yl)phosphonates,
as
well
ethyl
trans-(4-hydroxy-1,2,3,4-tetrahydroquinolin-2-yl)phenylphosphinates.
The
main
feature
this
is
regioselective
1,4-phosponylation
to
N-Cbz
quinolin-4(1H)-one
using
phosphite
or
phenylphosphinate
followed
by
highly
diastereoselective
reduction
give
cis
stereoisomers
favored
products,
which
were
converted
into
trans
through
Mitsunobu
reaction.
Cleavage
bond
under
hydrogenolysis
gave
target
heterocyclic
α-aminophosphonates
α-aminophosphinates.
Topics in Current Chemistry,
Journal Year:
2023,
Volume and Issue:
381(4)
Published: May 30, 2023
Abstract
Nitrogen
heterocycles
are
part
of
the
structure
natural
products
and
agents
with
important
biological
activity,
such
as
antiviral,
antibiotic,
antitumor
drugs.
For
this
reason,
heterocyclic
compounds
one
today’s
most
desirable
synthetic
targets
Povarov
reaction
is
a
powerful
tool
for
construction
highly
functionalized
systems.
This
process
involves
an
aromatic
amine,
carbonyl
compound,
olefin
or
acetylene
to
give
rise
formation
nitrogen-containing
heterocycle.
review
illustrates
advances
in
aspects
intramolecular
intricate
polyheterocyclic
compounds.
original
presents
research
done
field,
references
works
by
internationally
relevant
groups
on
current
topic,
covering
literature
from
1992
2022.
The
reactions
described
here
according
key
processes
involved,
using
different
combinations
heteroaromatic
amines,
aliphatic,
aromatic,
aldehydes.
Some
catalytic
promoted
transition
metals
detailed,
well
oxidative
some
asymmetric
processes.
Reaction Chemistry & Engineering,
Journal Year:
2023,
Volume and Issue:
8(8), P. 1969 - 1980
Published: Jan. 1, 2023
Furfural
is
a
versatile,
high-value-added
platform
molecule
that
can
be
produced
from
five
carbon
atom
(C5)
carbohydrates
present
in
lignocellulosic
biomass.
Current Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
28(13), P. 1023 - 1045
Published: March 19, 2024
Abstract:
The
reactivity
of
aldehydes
and
ketones
carries
great
potential
for
multicomponent
heterocyclizations.
These
reactions
are
convergent
highly
versatile
in
the
development
synthetic
methodologies
compound
families,
displaying
variations
substituents
their
structures.
Therefore,
they
have
been
regarded
as
an
important
tool
field
Green
Chemistry.
Furthermore,
prove
to
be
very
useful
studies
biological
activity,
where
small
structural
modifications
can
result
significant
differences.
Many
heterocyclizations
date
back
mid-19th
early
20th
centuries.
In
this
review,
we
aim
demonstrate,
through
some
these
reactions,
continuously
growing
improvements
concerning
development.
Additionally,
present
original
reported,
enabling
us
appreciate
evolution
chemical
representations
over
years
until
reaching
standardization
today.
Beilstein Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
21, P. 564 - 595
Published: March 13, 2025
Formaldehyde
emerges
as
a
cornerstone
in
multicomponent
reactions,
mainly
prized
for
its
robust
reactivity.
Yet,
alongside
these
beneficial
traits,
this
highly
reactive
C1-building
block
raises
concerns,
primarily
regarding
toxicity.
One
notable
issue
is
the
challenge
of
controlling
formation
undesired
byproducts
during
reactions.
This
review
explores
alternative
blocks
that
serve
surrogates
formaldehyde,
aiming
to
mitigate
some
challenges
associated
with
use
By
identifying
alternatives,
toxicity
concerns
and
improved
reaction
control
can
be
addressed,
paving
way
more
efficient
sustainable
synthetic
methodologies.
Chemistry - A European Journal,
Journal Year:
2022,
Volume and Issue:
29(15)
Published: Dec. 16, 2022
In
the
chalcogen
series,
tellurium
species
exhibit
strongest
bonding
(ChB)
interaction
with
electron-rich
atom.
This
property
explains
renewed
interested
toward
tellurium-based
derivatives
and
their
use
in
different
applications,
such
as
organocatalysis.
this
context,
catalytic
activity
of
telluronium
salts
Povarov
reaction
is
presented
herein.
Different
dienophiles,
well
imines
variable
electronic
nature,
efficiently
react
presence
amount
either
diarylmethyltelluronium
or
triaryltelluronium
salts.
Both
catalysts
could
also
readily
perform
three-component
starting
from
aldehyde,
aniline
dihydrofuran.
The
reactivity
telluroniums
towards
aldehydes
was
confirmed
solid
state
by
ability
Te
atom
to
interact
through
ChB
oxygen
carbonyl
acetone,
solution
significant
shift
variations
imine
proton
1
H
125
NMR
spectroscopy.
For
most
active
bearing
CF3
groups,
association
constants
(K)
N-phenyl
phenylmethanimine
range
22-38
M-1
were
measured
dichloromethane.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(2), P. 1099 - 1107
Published: Jan. 4, 2024
A
cornerstone
in
drug
discovery
is
the
development
of
strategies
to
provide
privileged
small
molecules
with
specific
structural
and
stereochemical
complexity,
allowing
access
new
potential
therapeutic
entities.
In
this
work,
a
strategy
based
on
[4
+
2]
Povarov
reaction
involving
1,3-diazadiene
was
developed.
This
approach
applied
for
straightforward
procedure
preparation
chromeno[4,3-d]pyrido[1,2-a]pyrimidine
derivatives,
accessible
substrates,
2-aminopyridine
unsaturated
aldehydes,
excellent
atom
economy
obtain
four
fused
ring
heterocycles,
regio-
diastereoselective
way.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(13), P. 3010 - 3021
Published: May 1, 2024
Abstract
Herein,
the
synthesis
of
homoallylic
amines,
quinolines,
and
tetrahydroquinolines
has
been
demonstrated.
The
domino
one‐pot
multi‐component
approach
accomplished
using
Lewis
acid‐catalyzed
conditions.
A
useful
scaffold
construction
strategy
can
be
achieved
by
controlling
electronic
effect
aniline
rather
than
relying
on
reaction
described
method
applies
to
a
wide
variety
substrates
embedded
with
diverse
functional
groups
extended
toward
natural
products.
Suitable
control
experiments,
real‐time
NMR
studies,
DFT
calculations
have
validated
reported
process.
protocol
outlines
for
synthesizing
amines
controlled
properties
anilines.
