Synthesis of Highly Fluorescent Thiazole Fused Benzo[a] Carbazoles by Sunlight Driven Photocyclization of Indolylthiazoles
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 19, 2024
Abstract
Herein
we
report
for
the
first
time
a
sunlight‐driven,
irreversible
photocyclization
reaction
of
indole‐linked
trisubstituted
thiazoles,
synthesis
highly
fluorescent
thiazole‐fused
benzo[
]carbazoles
using
mixture
solvents
(CH
3
CN:
DMSO;
:
1).
Ring
opening
indole
moiety
was
observed
in
case
thiazole
derivatives
having
2‐methyl
substituents.
Under
similar
conditions,
thiazoles
cyclic
1,3‐dicarbonyls
place
also
worked.
This
provides
products
two
medicinally
important
moieties
and
benzocarbazoles.
We
have
studied
photophysical
properties
all
found
that
most
synthesized
very
good
fluorescence
quantum
yields.
Язык: Английский
Iodine‐Catalyzed Cascade Reaction of 2‐Styrylbenzaldehydes with Indoles in the Synthesis of 1H‐Indenes via 4π‐Electrocyclization
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(6), С. 1436 - 1441
Опубликована: Янв. 23, 2024
Abstract
A
cascade
reaction
between
2‐styrylbenzaldehydes
and
indoles
has
been
developed
for
the
synthesis
of
1
H
‐indenes.
An
iodine‐catalyzed
nucleophilic
addition
to
an
aldehyde
group
leads
formation
carbocation
intermediates
that
undergo
4π‐electrocyclization
give
indenes
with
a
trisubstituted
double
bond.
These
are
transformed
into
thermodynamically
more
stable
products
fully
substituted
bond
under
conditions.
Minor
quantities
indolylbenzo[
b
]carbazoles
also
produced
as
by‐products.
Язык: Английский
Iodine-Catalyzed Regioselective Synthesis of Diphenyl-Substituted Carbazoles via [4 + 2] Annulation of β-Formyl Ketones with Indoles
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(24), С. 17505 - 17510
Опубликована: Ноя. 30, 2023
The
[4
+
2]
annulation
of
β-formyl
ketones
with
an
indole
has
been
developed
for
the
regioselective
synthesis
diphenyl-substituted
carbazoles
in
presence
a
catalytic
amount
iodine.
1,4-dicarbonyl
compound
containing
phenyl
group
at
α-position
aldehyde
reacts
more
readily
indoles
to
form
carbazole
derivatives.
Using
this
method,
variety
derivatives
can
be
accessed
under
mild
reaction
conditions.
Язык: Английский
Preparation of Carbazoles Involving 6π‐Electrocyclization, Photoredox‐, Electrochemical‐, and Thermal Cyclization Reactions: Mechanistic Insights
Chemistry - A European Journal,
Год журнала:
2023,
Номер
30(8)
Опубликована: Ноя. 30, 2023
Carbazole
is
a
heterocyclic
motif
that
can
be
found
in
diverse
array
of
natural
and
unnatural
products
displaying
wide
range
biological
physiological
properties.
Furthermore,
this
heterocycle
part
electronic
materials
like
photoconducting
polymers
organic
optoelectronic
owing
to
its
excellent
photophysical
characteristics.
Consequently,
the
development
synthetic
strategies
for
carbazole
scaffolds
holds
potential
significance
material
fields.
In
regard,
variety
preparation
methods
has
been
developed
exploit
their
efficient
distinct
formation
new
C-C
C-heteroatom
bonds
under
mild
conditions
enabling
broad
substrate
diversity
functional
group
tolerance.
Therefore,
review
focuses
on
synthesis
set
derivatives
describing
methodologies
involve
direct
irradiation,
photosensitization,
photoredox,
electrochemical
thermal
cyclization
reactions.
Язык: Английский
Dibenzo‐Fused Heterocycles: A Decade Update on the Syntheses of Carbazole, Dibenzofuran, and Dibenzothiophene
The Chemical Record,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 6, 2024
Abstract
Polycyclic
heterocycles
are
the
most
common
and
critical
structural
motifs
found
in
a
variety
of
natural
products,
medicines,
fertilizers,
advanced
materials.
Because
their
widespread
use
biologically
active
compounds
material
chemistry,
functionalised
dibenzo
heterocyclic
compounds,
especially
dibenzofuran,
dibenzothiophene,
carbazole
derivatives,
garnered
much
attention
over
time.
Scientists
interested
elucidating
more
efficient
techniques
for
developing
these
industrially
essential
compounds.
Dibenzo‐fused
can
rapidly
be
synthesised
using
highly
transition
metal‐catalysed
strategies
as
well
by
economic
metal‐free
reaction
conditions.
This
review
includes
detailed
overview
recent
significant
synthetic
techniques,
both
metal‐free,
to
produce
medicinally
important
dibenzo‐fused
heterocycles.
Язык: Английский
Indole Substrates to Carbazole Targets: An Update in the Discovery of an Ideal Synthetic Methodology
Journal of Molecular and Engineering Materials,
Год журнала:
2023,
Номер
11(03n04)
Опубликована: Ноя. 15, 2023
Carbazole
compounds
have
been
proven
to
exhibit
vital
photophysical
and
biological
applications.
Even
simple
carbazole
derivatives
were
showing
attractive
activities
such
as
antimicrobacterial
activity
(Glycozoline),
antiproliferative
(Mukonine),
free
radical
scavenger
(Carazostatin),
etc.
In
case
of
applications,
utilized
in
organic
semiconductors,
photoconducting
polymers,
Green
host
material
phosphorescent
light-emitting
diodes
(OLEDs),
hole-transporting
OLEDs
light
emitting
materials.
An
account
different
synthetic
methodologies
involved
the
synthesis
natural
was
evaluated
based
on
usage
commercially
available
cheap
starting
materials
Indole.
This
paper
takes
into
time
from
2011
2023.
The
advanced
methods
developed
12
principles
chemistry
Multistep
domino
reactions,
Atom
&
Step
economy
protection-free
mild
reaction
conditions,
open
atmosphere
harmless
by-products
photochemical
transformations.
Язык: Английский
One-pot and metal-free synthesis of atropisomeric carbazolyl-indoles by a facile [4 + 2]-benzannulation in ethanol and investigation of their photoluminescence property
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(12), С. 3397 - 3403
Опубликована: Янв. 1, 2024
In
this
article,
a
series
of
atropisomeric
carbazolyl-indoles
were
synthesized
through
one-pot,
green
method,
and
their
photoluminescence
properties
investigated.
Язык: Английский
Au(i)/Sc(iii)-co-catalyzed tandem spiroannulation/cycloisomerization of 3-(2-ethynylaryl)-N-tosylaziridines with indoles to access 5H-benzo[b]carbazoles
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(29), С. 5999 - 6003
Опубликована: Янв. 1, 2024
An
unusual
Au(
i
)/Sc(
iii
)-co-catalyzed
tandem
spiroannulation/cycloisomerization
of
3-(2-ethynylaryl)-
N
-tosylaziridine-2,2-diesters
with
indoles
has
been
reported.
A
variety
5
H
-benzo[
b
]carbazoles
were
obtained
in
moderate
to
good
yields
(30–88%).
Язык: Английский