Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthons
Green Synthesis and Catalysis,
Год журнала:
2022,
Номер
4(3), С. 258 - 262
Опубликована: Май 10, 2022
The
first
diastereodivergent
formal
[4
+
1]
cycloaddition
reactions
of
azoalkenes
with
p-quinone
methides
(p-QMs)
have
been
accomplished.
reported
reaction
occurred
via
a
domino
oxa-1,4-addition/1,6-addition
process,
allowing
the
use
common
as
C1
synthons.
A
broad
range
2,3-dihydrobenzofurans
was
smoothly
prepared
in
good
yields
and
reversible
diastereoselectivities.
steric
hindrance
hydrogen-bonding
interaction
were
proposed
to
account
for
two
different
modes
diastereo-control.
projected
features
employment
azoalkene
carbene-like
synthon,
mild
conditions,
substrate
scope
tunable
diastereoselectivity.
Язык: Английский
Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis
Molecules,
Год журнала:
2022,
Номер
27(19), С. 6708 - 6708
Опубликована: Окт. 9, 2022
Many
heterocyclic
compounds
can
be
synthetized
using
diaza-1,3-butadienes
(DADs)
as
key
structural
precursors.
Isolated
and
in
situ
diaza-1,3-butadienes,
produced
from
their
respective
precursors
(typically
imines
hydrazones)
under
a
variety
of
conditions,
both
react
with
wide
range
substrates
many
kinds
reactions.
Most
these
reactions
discussed
here
include
nucleophilic
additions,
Michael-type
reactions,
cycloadditions,
Diels–Alder,
inverse
electron
demand
aza-Diels–Alder
This
review
focuses
on
the
reports
during
last
10
years
employing
1,2-diaza-,
1,3-diaza-,
2,3-diaza-,
1,4-diaza-1,3-butadienes
intermediates
to
synthesize
heterocycles
such
indole,
pyrazole,
1,2,3-triazole,
imidazoline,
pyrimidinone,
pyrazoline,
-lactam,
imidazolidine,
among
others.
Fused
heterocycles,
quinazoline,
isoquinoline,
dihydroquinoxaline
derivatives,
are
also
included
review.
Язык: Английский
Easy Access to Indole‐based Bi‐Sulfurylate‐Heterocyclic Scaffolds
Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(9)
Опубликована: Июнь 9, 2022
Abstract
New
and
valuable
indole
based
sulfurylated
bi‐heterocyclic
systems
such
as
4‐((1
H
‐indol‐2‐yl)thio)‐5‐oxo‐4,5‐dihydro‐1
‐pyrazoles
3,3‐dimethyl‐3′
‐spiro‐indoline‐2,2′‐thiazoles
are
regioselectively
obtained
under
very
mild
conditions
employing
1,2‐diaza‐1,3‐dienes
not
smelly
indoline
2‐thiones
starting
materials.
Язык: Английский
Challenge N- versus O-six-membered annulation: FeCl3-catalyzed synthesis of heterocyclic N,O-aminals
Beilstein Journal of Organic Chemistry,
Год журнала:
2024,
Номер
20, С. 1412 - 1420
Опубликована: Июнь 26, 2024
A
new
class
of
heterocyclic
N
,
O
-aminal
and
hemiaminal
scaffolds
was
successfully
obtained
by
means
a
three-component
reaction
(3-CR)
1,2-diaza-1,3-dienes
(DDs),
α-aminoacetals
iso(thio)cyanates.
These
stable
imine
surrogates
are
generated
from
key-substituted
(thio)hydantoin
intermediates
through
selective
FeCl
3
-catalyzed
intramolecular
-annulation.
Язык: Английский
1,2‐Diaza‐1,3‐dienes as a Multifaceted Synthon for the Synthesis of Heterocycles: A Fifteen‐Years Update
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(44)
Опубликована: Авг. 9, 2024
Abstract
The
discovery
of
structurally
unique
scaffolds
entities
with
increased
complexity
and
balanced
physicochemical
properties
has
the
potential
to
allow
synthetic
chemists
exploit
areas
chemical
space
that
were
previously
inaccessible.
Among
different
strategies
employed
for
generating
N
‐heterocycles,
cyclization
cycloaddition
reactions
represent
a
valuable
tool.
purpose
this
minireview
is
summarize
recent
advances
(2009‐present)
from
our
laboratory
on
generation
intriguing
five‐,
six‐
seven‐membered
mono‐
or
poly‐heterocyclic
architectures
(linear,
fused
spiro)
employing
1,2‐diaza‐1,3‐dienes
(DDs)
as
key
synthons.
Язык: Английский