Advances in the Synthesis of Heterocycles with Two and Three Heteroatoms using Hydrazonoyl Halides
Helvetica Chimica Acta,
Год журнала:
2024,
Номер
107(7)
Опубликована: Апрель 30, 2024
Abstract
The
review
covers
the
results
of
studies
published
in
literature
on
use
hydrazonoyl
halides
synthesis
five‐
(pyrazoles,
thiazoles,
triazoles,
oxa‐
and
thiadiazoles),
six‐
(oxa‐
thiadiazines,
indazoles,
pyridazines,
pyrazines,
tetrazines)
or
seven‐membered
(benzotriazepine)
heterocycles.
In
formation
these
heterocycles,
main
intermediate
stage
reaction
is
situ
generation
nitrilimine,
which
enters
into
a
cycloaddition
with
substituted
acetylenes
(including
generated
benzynes,
naphthynes),
allenes,
activated
olefins,
anthranilic
acid
derivatives,
organosulfur
compounds
(mercaptoaldehydes,
mercaptocarboxylic
acids)
fused
Examples
are
given
heterocycles
by
replacing
halogen
atom
from
halide
molecule
nucleophilic
group,
followed
exhaustive
intramolecular
cyclization
target
compound.
There
discussions
reactions
nitrilimine
to
synthesized
Knoevenagel
condensation
product
(from
CH‐acid
compounds,
such
as
di‐
monocarbonyl
dinitrile
malonic
acid)
occurs,
leading
spiro‐linked
conventional
pyrazoles.
Some
syntheses
biologically
active
representatives
shown.
Язык: Английский
Organocatalytic multicomponent coupling to access a highly functionalised tetracyclic furoindoline: interrupted Passerini/Joullié–Ugi cascade reaction
Chemical Communications,
Год журнала:
2022,
Номер
58(83), С. 11701 - 11704
Опубликована: Янв. 1, 2022
The
interrupted
Passerini
reaction
of
3-(2-isocyanoethyl)-indole
catalysed
by
3,5,6-trifluoro-2-pyridone
is
described.
diastereoselectively
provided
a
tetracyclic
furolindoline,
which
proved
to
be
good
substrate
for
the
Joullié-Ugi
reaction;
therefore,
sequential
Passerini/Joullié-Ugi
reactions
were
performed
in
one-pot
rapidly
provide
versatile
and
highly
functionalised
furoindolines
from
3-(2-isocyanoethyl)-indole.
Язык: Английский
Divergent synthesis of new naphtho-fused 2-aminoindolines and naphthoxindoles based on straightforward construction of phenanthrene
Green Synthesis and Catalysis,
Год журнала:
2023,
Номер
unknown
Опубликована: Ноя. 1, 2023
An
environmentally
friendly,
highly
atom-economical
and
operationally
simple
approach
toward
the
synthesis
of
naphtho-fused
2-aminoindolines
naphthoxindoles
starting
from
biaryl
aldehydes
secondary
amines
has
been
developed.
This
notable
methodology
integrates
consecutive
intramolecular
Mannich-type
cyclization
triggered
by
dearomatization
indole
with
subsequent
aromatization
via
β-elimination
then
amination
or
oxidation
at
C2-position
nucleus.
The
amine-controlled
divergent
protocol
together
an
easy
product
isolation
process
provides
a
practical
route
for
first
time
to
access
2-substituted
indoline.
Язык: Английский