Benzannulation of Functionally Enhanced Indole-3-carbaldehydes with Ynones and Alkynoates: A Domino Approach to Bioactive Carbazoles─Synthesis of Clauolenzole A, Calothrixin A & B, Methyl Carbazole-3-carboxylate, and Quinocarbazole
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 5, 2025
A
flexible,
regioselective,
benzannulation
strategy
toward
multifunctional
carbazoles
from
2-(2-oxo-2-arylethyl)indole-3-carbaldehydes,
employing
either
ynones
or
alkynoates
as
reaction
partners,
has
been
envisaged
and
implemented.
This
enabling
access
to
variegated
in
one-flask
operation
leads
strategic
substituent
diversification
via
partner
variation.
The
efficacy
applications
of
this
methodology
are
demonstrated
through
23
examples
concise
syntheses
bioactive
clauolenzole
A,
calothrixin
&
B,
methyl
carbazole-3-carboxylate,
pharmacophoric
quinocarbazole.
Язык: Английский
An Expedient Flow Chemistry Approach to Substituted 1,4‐Dimethylcarbazoles
ChemistrySelect,
Год журнала:
2025,
Номер
10(13)
Опубликована: Март 28, 2025
Abstract
A
simple,
expedient
continuously
scalable
flow
chemistry
synthesis
of
a
range
1,4‐dimethylcarbazoles
from
substituted
indoles
and
2,5‐hexanedione
in
the
presence
K‐10
(montmorillonite
clay)
is
reported.
Optimization
conditions
led
to
development
an
in‐house
K‐10/sand
Omnifit
TM
catalyst
column
that
at
140
°C
0.4
mL.min
−1
afforded
>90%
conversion
selected
indole
desired
1,4‐carbazole.
This
equates
ca
80
mg.h
production
rate.
The
reaction
was
tolerant
electron
donating
but
not
withdrawing
indoles.
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
Photocatalyzed cascade hydrogen atom transfer for the construction of α-CF3-1,4-diketones
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 5, 2024
A
TBADT-photocatalyzed
cascade
hydrogen
atom
transfer
procedure
was
established
for
the
synthesis
of
α-CF
3
-1,4-diketones
from
aldehydes
and
2-bromo-3,3,3-trifluoro-1-propenes.
Язык: Английский