Controllable methylenation with ethylene glycol as the methylene source: bridging enaminones and synthesis of tetrahydropyrimidines
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(21), С. 5935 - 5941
Опубликована: Янв. 1, 2022
Controllable
methylenation
using
renewable
ethylene
glycol
as
the
methylene
source
has
been
developed
for
introduction
of
one
or
two
building
blocks.
Язык: Английский
Acidic Deep Eutectic Solvents as Active Media for Sustainable Synthesis of Biindoles Starting from 2,2’‐Diaminotolanes and Aldehydes
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(16)
Опубликована: Март 20, 2023
Abstract
We
describe
an
alternative
and
more
sustainable
method
for
the
synthesis
of
2,2’‐disubstituted
3,3’‐biindoles
starting
from
2,2’‐diaminotolanes
(hetero)arylaldehydes.
The
key
feature
approach
is
use
acidic
Deep
Eutectic
Solvent
(DES)
able
to
exploit
a
double
activity,
i.
e.,
solvent
Brønsted
Acid
(BA)
catalyst,
avoiding
Volatile
Organic
Compounds
(VOCs)
as
solvents
additional
acid
catalysts.
By
this
way,
we
synthesized
twenty‐five
biindoles,
including
eighteen
new
compounds.
reactions
run
quickly
under
mild
conditions
by
microwave
heating
at
70
°C,
with
yields
ranging
good
very
good.
reaction
scope
rather
broad.
medium
demonstrated
be
reusable
least
five
times
only
slight
reduction
in
yields.
Based
on
experimental
evidence
previous
literature
findings,
plausible
mechanism
proposed.
Язык: Английский
Electrochemical Cyclization of Alkynyl Enaminones: Controllable Synthesis of Indeno[1,2-c]pyrroles or Indanones
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(16), С. 11131 - 11140
Опубликована: Авг. 4, 2022
We
report
an
electrochemical
intramolecular
[3
+
2]
cyclization
of
alkynyl
enaminones
in
a
user-friendly
undivided
cell
under
constant
current
conditions
without
oxidant
and
catalyst,
indeno[1,2-c]pyrrole
derivatives
could
be
obtained
good
to
excellent
yields.
Notably,
preliminary
substituent-controlled
selective
transformation
is
also
achieved
electrocatalysis
alone,
(R4
≠
H)
or
indanone
=
prepared
directly
adding
base
heating
process.
Язык: Английский
Brønsted Acid-Catalyzed Synthesis of 4-Functionalized Tetrahydrocarbazol-1-ones from 1,4-Dicarbonylindole Derivatives
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(1), С. 505 - 520
Опубликована: Дек. 12, 2023
A
p-toluenesulfonic
acid-catalyzed
cascade
reaction
is
reported
for
the
synthesis
of
4-functionalized
tetrahydrocarbazolones
via
4-(indol-2-yl)-4-oxobutanal
derivatives
with
a
variety
nucleophiles
in
acetonitrile
or
hexafluoroisopropanol.
After
initial
intramolecular
Friedel–Crafts
hydroxyalkylation,
3-indolylmethanol
intermediate
subsequently
activated
and
reacted
external
nucleophile.
The
conditions
are
crucial
to
avoid
alternative
pathways,
allowing
direct
substitution
thiols,
(hetero)arenes,
alkenes,
sulfinates.
procedure
features
high
overall
yields
access
diverse
family
compounds
bearing
tetrahydrocarbazole
core.
Язык: Английский
Selectfluor-Mediated Oxidative Dehydrogenation of Hydrazines: A Process for the Synthesis of Azo Compounds
Synthesis,
Год журнала:
2022,
Номер
54(23), С. 5245 - 5252
Опубликована: Июль 13, 2022
Abstract
A
facile
method
to
synthesize
azo
compounds
from
hydrazine
derivatives
is
developed.
This
represents
the
unprecedented
example
of
Selectfluor-mediated
oxidative
dehydrogenation
derivatives.
The
reaction
might
proceed
through
N-fluorination
and
elimination
processes.
protocol
exhibits
key
features
including
simple
operation,
mild
conditions,
good
functional
group
tolerance,
high
efficiency.
Moreover,
advantage
also
highlighted
by
conversion
a
sulfonyl-substituted
compound
furnish
acetanilide
in
excellent
yield
under
4
W
blue
LED
irradiation.
Язык: Английский