Current Organic Chemistry,
Год журнала:
2023,
Номер
27(12), С. 997 - 1009
Опубликована: Июнь 1, 2023
Abstract:
Nitrogen
ring
junction
heterocycles
play
a
crucial
role
in
synthetic
organic
chemistry
due
to
their
remarkable
activity.
The
fused
nitrogen
compounds
are
abundant
nature;
they
have
excellent
biological
activity
and
used
against
various
health
issues.
To
make
selective
products
from
the
heterocycles,
expensive
chemicals
catalysts,
like
transition
metal
complexes
composites,
required.
neglect
drawbacks
of
conventional
synthesis
methods
long
reaction
times,
by-product
formation,
lower
selectivity,
low
yields,
an
alternative
nonconventional
light-mediated
techniques
can
be
opted
for.
light
source
uses
radical
mechanism
that
reduces
provides
regio-selective
product,
increases
yield,
decreases
time,
is
cost-effective,
does
not
require
special
catalysts
or
chemicals.
There
variety
sources,
viz.,
UV,
visible,
IR,
laser,
X-ray.
visible
light,
white,
green,
blue
LED
sources
widely
photochemical
method.
This
review
emphasizes
nitrogen-ring
heterocyclic
compounds.
ACS Catalysis,
Год журнала:
2024,
Номер
14(7), С. 4856 - 4864
Опубликована: Март 18, 2024
Pyrroles
are
important
N-heterocycles
found
in
medicines
and
materials.
The
formation
of
pyrroles
from
widely
accessible
pyrrolidines
is
a
potentially
attractive
strategy
but
an
underdeveloped
approach
due
to
the
sensitivity
oxidative
conditions
required
achieve
such
transformation.
Herein,
we
report
catalytic
that
employs
commercially
available
B(C6F5)3
operationally
simple
procedure
allows
serve
as
direct
synthons
for
pyrroles.
Mechanistic
studies
have
revealed
insights
into
borane-catalyzed
dehydrogenative
processes.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(7), С. 4530 - 4537
Опубликована: Март 14, 2024
A
copper-catalyzed
method
for
the
dehydrogenation
of
various
nitrogen-containing
heterocycles
to
furnish
quinolines
and
indoles
has
been
developed.
range
1,2,3,4-tetrahydroquinolines
underwent
by
employing
2
mol
%
copper
complex
Cat
3
as
a
catalyst
using
O2
an
oxidant
at
120
°C
in
1,2-dichlorobenzene
afford
desired
quinolines.
The
enables
variety
indolines
presence
2,
10
TEMPO
additive
under
room
temperature
tetrahydrofuran
high
yields.
Mechanistic
studies
suggested
that
dehydrogenative
activity
is
ascribed
formation
copper(II)
active
species
from
copper(I)
complexes
oxidized
O2,
which
was
proved
high-resolution
mass
spectrometry
(HRMS).
reaction
proceeds
via
superoxide
radical
anion
(·O2–)
electron
paramagnetic
resonance
(EPR)
spectrometry.
In
situ
infrared
spectroscopy
revealed
dihydroquinoline
intermediate
formed
1,2,3,4-tetrahydroquinolines.
Chemical Communications,
Год журнала:
2021,
Номер
58(1), С. 10 - 28
Опубликована: Ноя. 18, 2021
N-Heteroarenes
are
widely
used
for
numerous
medicinal
applications,
lifesaving
drugs
and
show
utmost
importance
as
intermediates
in
chemical
synthesis.
This
feature
article
highlights
the
recent
advances,
from
2015
to
August
2021,
on
sp2
sp3
C-H
bond
functionalization
reactions
of
various
N-heteroarenes
catalyzed
by
non-precious
transition
metals
(Mn,
Co,
Fe,
Ni,
etc.).
The
salient
features
report
are:
(i)
development
newer
catalysis
Csp2-H
activation
categorized
into
alkylation,
alkenylation,
borylation,
cyanation,
annulation
reactions,
(ii)
advances
Csp3-H
considering
approaches
alkylation
well
alkenylation
processes,
(iii)
synthetic
applications
practical
utility
catalytic
protocols
utilized
late-stage
drug
development;
(iv)
scope
along
with
mechanistic
studies
detail
findings
important
processes.
SynOpen,
Год журнала:
2022,
Номер
06(04), С. 286 - 305
Опубликована: Авг. 24, 2022
Abstract
C–H
bond
functionalization
is
one
of
the
most
effective
strategies
for
rapid
synthesis
cyclic
amines
containing
substituents
on
ring,
which
are
core
structures
many
bioactive
molecules.
However,
it
much
more
challenging
to
perform
this
strategy
remote
bonds
compared
α-C–H
amines.
This
graphical
review
aims
provide
a
concise
overview
transition-metal-catalyzed
methods
Examples
categorized
and
demonstrated
according
mechanistic
pathways
that
initiate
reactions
amine
substrates.
Where
relevant,
selected
substrate
scope
detailed
reaction
mechanisms
given.
Abstract
We
herein
reported
a
general
and
efficient
Ni‐catalyzed
protocol
for
sequential
double
de‐hydrogenative
cyclization
of
2‐amino(nitro)‐benzyl
alcohols
with
primary
to
C‐3‐substituted
quinolines
releasing
water
dihydrogen
as
by
products.
As
special
highlight,
late
stage
functionalization
cholesterol
derivative
including
chemo‐selective
transformations
citronellol,
fatty
acid
derived
oleyl
alcohol
long
chain
C
4
−C
14
alkyl
were
reported.
Initial
mechanistic
studies
deuterium‐labelling
experiments
perform
establish
the
cyclization.
