The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(17), P. 12387 - 12391
Published: Aug. 22, 2024
A
novel
method
has
been
developed
for
the
synthesis
of
1,3-thiazin-4-one
compounds
containing
trifluoromethyl
groups
utilizing
2-trifluoromethyl
acrylic
acid
and
thioamides
as
key
starting
materials.
This
protocol
is
characterized
by
its
simplicity,
practicality,
tolerance
toward
various
functional
groups.
Given
straightforward
nature
procedure,
ready
availability
both
materials,
significance
drugs
trifluoromethyl,
it
anticipated
that
this
reaction
will
have
wide-ranging
applications.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(31), P. 12473 - 12479
Published: Jan. 1, 2024
Bicyclo[1.1.0]butanes
(BCBs),
featuring
two
fused
cyclopropane
rings,
have
found
widespread
application
in
organic
synthesis.
Their
versatile
reactivity
towards
radicals,
nucleophiles,
cations,
and
carbenes
makes
them
suitable
for
various
reactions,
including
ring-opening
annulation
strategies.
Despite
this
versatility,
their
potential
as
enophiles
an
ene
reaction
remains
underexplored.
Considering
given
the
challenges
of
achieving
diastereoselectivity
reactions
BCBs,
herein,
we
present
a
unique
method
utilizing
BCBs
mild
diastereoselective
Sc(OTf)
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 20, 2025
Lewis
acid-enabled
reactions
of
donor-acceptor
cyclopropanes
(DACs)
with
indoline-2-thiones
are
reported.
The
reaction
exhibits
tunable
annulation
depending
on
the
acid
and
substituent
at
N1
indoline-2-thiones.
With
AlCl3
as
1-isopropylindoline-2-thiones
reactants,
a
direct
ring
opening
DACs,
followed
by
intramolecular
nucleophilic
addition/dehydration
takes
place
leading
to
formation
dihydro-2H-thiepino[2,3-b]indoles
in
moderate
good
yields.
Using
Yb(OTf)3
promoter
1-unsubstituted
(3
+
2)
cycloaddition
DACs
accompanied
sulfur
rearrangement
give
3-indolyl-4,5-dihydrothiophenes
In
addition,
synthetic
transformation
3-indolyl-4,5-dihydrothiophene
sulfone
indole-based
axially
chiral
scaffolds
further
extends
utility
structural
complexity.
Synthesis,
Journal Year:
2023,
Volume and Issue:
55(23), P. 3875 - 3894
Published: May 22, 2023
Abstract
This
review
discusses
the
utility
of
donor-acceptor
cyclopropanes
(DACs)
for
construction
heterocycles.
In
addition
to
(3+2),
(3+3),
and
(4+3)
cycloaddition
pathways,
nucleophilic
ring-opening
reactions,
intramolecular
transformations,
cycloisomerizations
in
presence
suitable
catalysts
pave
way
generation
heterocycles
from
DACs.
The
mild
reactions
conditions
employed
variety
starting
materials
that
can
be
used
as
reaction
partners
make
DAC
route
heterocycle
synthesis
attractive.
literature
covered
this
is
period
2018
2023.
1
Introduction
2
Synthesis
Nitrogen
Heterocycles
2.1
By
Annulations
with
Anthranils
Azadienes
2.2
Nucleophilic
Attack
Anilines
Hydrazones
2.3
Reaction
Ureas
Thioureas
2.4
Annulation
Reactions
Using
an
Azomethine
Imine
2.5
Other
2.6
Transformations
3
Oxygen
3.1
Intramolecular
3.2
Intermolecular
4
Sulfur
Selenium
4.1
Thiocarbonyl
Substrates
4.2
Thio-
Selenocyanates
Thiosulfonate
Salts
5
N–S
N–O
6
Conclusions
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(8), P. 1672 - 1676
Published: Feb. 15, 2024
The
(3
+
2)
cycloaddition/sulfur
rearrangement
reaction
of
donor–acceptor
cyclopropanes
bearing
a
single
keto
acceptor
with
indoline-2-thiones
has
been
realized.
Under
the
catalysis
Sn(OTf)2,
series
functionalized
3-indolyl-4,5-dihydrothiophenes
were
synthesized
moderate
to
excellent
yields.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(10), P. 1643 - 1648
Published: March 6, 2023
The
use
of
benzotriazoles
as
nucleophilic
triggers
in
the
three-component
Yb(OTf)3-catalyzed
ring-opening
1,3-aminofunctionalization
donor-acceptor
(D-A)
cyclopropanes
is
presented.
Using
N-halo
succinimide
(NXS)
third
component,
reaction
afforded
1,3-aminohalogenation
product
up
to
an
84%
yield.
Moreover,
using
alkyl
halides
or
Michael
acceptors
components,
3,1-carboaminated
products
are
formed
a
96%
yield
one-pot
operation.
Employing
Selectfluor
electrophile,
furnished
1,3-aminofluorinated
61%
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
88(1), P. 132 - 142
Published: Dec. 16, 2022
A
new
methodology
for
the
synthesis
of
N-haloindole-fused
dihydrothiopyrano
derivatives
via
(3
+
3)-annulation
donor-acceptor
cyclopropanes
(DACs)
with
indoline-2-thiones
in
presence
Sc(OTf)3
as
a
Lewis
acid
catalyst
has
been
developed.
This
protocol
provides
variety
indole-fused
molecules
good
to
excellent
yields,
which
architecturally
resemble
other
tricyclic
having
potential
medicinal
value.
In
addition,
we
have
described
detailed
reaction
mechanism
and
transformation
furnished
product
into
N-fused
thiazino
indole
molecule.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(20), P. 14587 - 14600
Published: Oct. 11, 2023
A
Yb(OTf)3-catalyzed
formal
(4
+
3)
cycloaddition
reaction
of
donor-acceptor
cyclopropanes
with
3-benzylideneindoline-2-thiones
as
sulfur-containing
4π
components
has
been
successfully
achieved.
series
functionalized
5,10-dihydro-2H-thiepino[2,3-b]indole
derivatives
were
synthesized
good
yields
and
moderate
to
diastereoselectivity.
The
described
herein
represented
the
inaugural
3-benzylideneindoline-2-thiones.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(10), P. 1685 - 1692
Published: May 5, 2023
Abstract
Installation
of
an
alkyl
chain
at
a
specified
position
in
the
aromatic
ring
via
metal‐free
catalysis
is
very
important.
In
this
regard,
we
have
developed
facile
metal‐free,
extremely
selective,
user‐friendly,
environmentally
benign
and
cost‐effective
Friedel‐Crafts
(FC)
alkylation
protocol
for
2‐oxindoles
anilines
with
donor‐acceptor
cyclopropanes.
Real‐time
NMR
studies
reveal
that
transformation
governed
by
cooperative
Brønsted
acid
(TfOH)
HFIP,
which
facilitates
nucleophilic
attack
on
cyclopropanes
from
anilines.
magnified
image
