The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(20), P. 14665 - 14672
Published: Sept. 23, 2024
We
have
developed
a
high
yielding
synthesis
of
indolizine
and
directly
elaborated
the
molecule
into
three
optically
active
indolizinylalanine
regioisomers.
The
protocols
exploit
metal
catalyzed
coupling
indolizinyl-halides
with
organozinc
reagents
derived
from
carbamoylated
iodoalanine
esters.
scalable
provide
products
in
form
amenable
to
solid-phase
peptide
(SPPS).
When
incorporated
peptides,
heterocycle
is
more
basic
markedly
less
nucleophilic
than
tryptophan.
Its
protonated
vinylpyridinium
deeply
colored
solution
while
neutral
highly
fluorescent.
fluorescence
quantum
yield
exceeds
that
indole
aza-indoles
water,
suggesting
indolizinylalanines
could
be
powerful
optical
probes
protein
structure
dynamics,
functioning
as
true
tryptophan
isosteres.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 15, 2025
We
report
a
novel
and
efficient
strategy
for
constructing
tetrasubstituted
alkenes
α-iminonitriles
from
3-aminoindolizines
3-aminoimidazo[1,2-a]pyridines.
This
approach
involves
dearomative
ring-opening
of
N-fused
heteroaromatic
amines
coupled
to
DDQ-mediated
oxidative
process
under
mild,
metal-free
conditions.
The
methodology
demonstrates
broad
substrate
scope,
excellent
functional
group
tolerance,
scalability,
offering
versatile
platform
synthesizing
complex
nitrile-containing
frameworks.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(12)
Published: Jan. 19, 2024
Abstract
A
catalytic
carbonylative
method
for
the
direct,
multicomponent
synthesis
of
indolizine
fluorophores
has
been
developed.
The
process
is
based
on
PdI
2
/KI‐catalyzed
oxidative
aminocarbonylation
2‐(pyridin‐2‐yl)pent‐4‐yn‐1‐carbonyl
compounds
leading
to
corresponding
2‐ynamide
intermediates,
followed
in
situ
by
5‐
exo
‐
dig
cyclization
(by
amine‐promoted
conjugate
addition
pyridine
ring
nitrogen)
and
aromatization,
give
finally
isolated
N
,
‐disubstituted
2‐(indolizin‐3‐yl)acetamides.
Reactions
are
carried
out
under
relatively
mild
conditions
(100
°C
20
atm
a
4
:
1
mixture
CO−air
6–15
h)
MeCN
as
solvent
with
low
catalyst
loading
(0.33
mol%
),
presence
0.5
equiv.
KI
3
secondary
amine.
optical
properties
representative
2‐(indolizin‐3‐yl)acetamide
products
have
also
investigated.
Molecules,
Journal Year:
2024,
Volume and Issue:
29(9), P. 2061 - 2061
Published: April 29, 2024
Herein,
we
have
developed
a
new
approach
for
the
synthesis
of
indolizine
via
Cu-catalyzed
reaction
pyridine,
acetophenone,
and
nitroolefin
under
mild
conditions
in
high
yields.
This
involved
formation
C–N
C–C
bonds
compounds
with
stereoselectivity
excellent
functional
group
tolerance.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(22)
Published: April 19, 2023
Abstract
This
work
investigates
a
light‐driven
3‐component
sulfonylation
reaction
of
indolizines
without
needing
any
external
photocatalyst.
The
mechanistic
investigations
support
the
formation
an
electron
donor–acceptor
(EDA)
complex
in
situ.
transformation
offers
mild
and
sustainable
approach
with
high
functional
group
tolerance
for
synthesis
3‐sulfonylated
indolizines.
compound
class
has
valuable
photophysical
properties
represents
promising
candidates
various
applications
related
to
fluorescence.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(13), P. 3685 - 3691
Published: Jan. 1, 2024
A
new
method
for
the
synthesis
of
seven-membered
heterocycle-fused
indolizine
scaffolds
from
2-(1-alkynyl-cyclopropyl)pyridines
and
nitrones
under
catalysis
PPh
3
AuNTf
2
.
