Exploring the capabilities of 2-alkynyl aryl/benzyl azides: synthesis approaches for indoles, quinolines, and their derivatives via transition metal catalysis
RSC Advances,
Journal Year:
2025,
Volume and Issue:
15(2), P. 1163 - 1204
Published: Jan. 1, 2025
This
review
covers
the
metal-catalyzed
transformation
of
2-alkynyl
aryl/benzyl
azides
into
indoles
and
quinolines
(2011–2024),
addressing
substrates,
recent
advancements,
research
challenges,
mechanisms
to
promote
further
research.
Language: Английский
Gold-Catalyzed Cascade Cycloisomerization of 3-Allyloxy-1,6-diynes to Cyclopropyl- and Cyclobutyl-Fused Benzofurans and Chromen-3a(1H)-ols
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(13), P. 2635 - 2640
Published: March 25, 2024
A
synthetic
method
for
the
efficient
preparation
of
partially
hydrogenated
benzo[f]cyclobuta[cd]cyclopenta[h]benzofurans
and
cyclopropa[c]chromen-3a(1H)-ols
that
relies
on
gold(I)-catalyzed
cascade
cycloisomerization
3-allyloxy-1,6-diynes
is
described.
Language: Английский
Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues
Molecules,
Journal Year:
2024,
Volume and Issue:
29(12), P. 2813 - 2813
Published: June 13, 2024
Aurones,
particular
polyphenolic
compounds
belonging
to
the
class
of
minor
flavonoids
and
overlooked
for
a
long
time,
have
gained
significative
attention
in
medicinal
chemistry
recent
years.
Indeed,
considering
their
unique
outstanding
biological
properties,
they
stand
out
as
an
intriguing
reservoir
new
potential
lead
drug
discovery
context.
Nevertheless,
several
physicochemical,
pharmacokinetic,
pharmacodynamic
(P3)
issues
hinder
progression
more
advanced
phases
pipeline,
making
optimization
campaigns
necessary.
In
this
context,
scaffold
hopping
has
proven
be
valuable
approach
natural
products.
This
review
provides
comprehensive
updated
picture
scaffold-hopping
approaches
directed
at
synthetic
aurones.
literature
analysis,
focus
is
given
nitrogen
sulfur
analogues.
For
each
presented,
general
procedures
are
summarized,
highlighting
key
advantages
issues.
Furthermore,
activities
most
representative
scaffold-hopped
emphasizing
improvements
achieved
further
compared
aurone
class.
Language: Английский
Gold‐Catalysed 1,2‐Difunctionalisation: Sulfoximines as N‐ and O‐Transfer Reagents
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 11, 2024
Abstract
Among
the
nucleophilic
oxidants
employed
in
gold‐catalysed
oxidation
of
alkynes,
sulphur‐based
reagents
have
played
a
substantial
role
since
beginning,
granting
access
to
respective
gold
carbene
intermediates.
Herein,
we
describe
first
example
substance
class
sulfoximines
being
used
as
atom
transfer
alkynes
catalysis.
Based
on
transformation
N
‐(2‐alkynylphenyl)
3
H
‐indol‐3‐ones,
it
is
demonstrated
that
sulfoximine
functionality
capable
selectively
transferring
its
nitrogen
moiety
alkyne,
forming
α‐imino
carbene,
which
then
oxidised
by
released
sulfoxide
second
step
via
pseudo‐intramolecular
mechanism—a
distinctive
feature
differentiates
this
work
mechanistically
from
earlier
studies.
A
combination
extensive
experimental
and
theoretical
studies
provides
evidence
for
mechanistic
rationale.
As
no
external
1,2‐difunctionalisation
alkyne
unit
are
required,
wide
variety
functional
groups
tolerated
transformation,
affording
desired
‐indol‐3‐ones
mostly
good
yields.
It
was
further
also
showcased
possible
combine
our
methodology
with
additional
transformations
‐indol‐3‐one
core
one‐pot
procedures,
allowing
facile
C2‐quaternary
indolin‐3‐one
structures.
Language: Английский
Gold‐Catalysed 1,2‐Difunctionalisation: Sulfoximines as N‐ and O‐Transfer Reagents
Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 11, 2024
Abstract
Unter
den
nukleophilen
Oxidationsmitteln,
die
bei
der
goldkatalysierten
Oxidation
von
Alkinen
eingesetzt
werden,
haben
schwefelbasierte
Reagenzien
Beginn
an
eine
wesentliche
Rolle
gespielt
und
ermöglichten
Zugang
zu
jeweiligen
Goldcarben
Intermediaten.
Wir
beschreiben
hier
das
erste
Beispiel
für
Verwendung
Substanzklasse
Sulfoximine
als
Atomtransferreagenzien
in
Goldkatalyse.
Anhand
Umwandlung
N
‐(2‐Alkinylphenyl)‐sulfoximinen
3
H
‐Indol‐3‐onen
wird
gezeigt,
dass
Sulfoximinfunktionalität
dazu
Lage
ist,
unter
Ausbildung
des
α‐Imino‐Goldcarbens
zunächst
Stickstoffeinheit
selektiv
auf
Alkin
übertragen,
welches
dann
einem
zweiten
Schritt
durch
freigesetzte
Sulfoxid
pseudo‐intramolekularen
Mechanismus
oxidiert
‐
Besonderheit,
diese
Arbeit
mechanistisch
früheren
Studien
unterscheidet.
Eine
Kombination
aus
umfangreichen
experimentellen
theoretischen
liefert
Beweise
zugrundeliegenden
Mechanismus.
Da
keine
externen
1,2‐Difunktionalisierung
Alkins
erforderlich
sind,
Vielzahl
funktioneller
Gruppen
toleriert,
so
gewünschten
‐Indol‐3‐one
meist
guter
Ausbeute
erhalten
werden.
Darüber
hinaus
wurde
es
möglich
unsere
Methodik
mit
weiteren
Transformationen
‐Indol‐3‐on
Kerns
Eintopfverfahren
kombinieren,
was
einen
einfachen
C2‐quartären
Indolin‐3‐on
Strukturen
ermöglicht.