Synthesis,
Journal Year:
2022,
Volume and Issue:
54(24), P. 5451 - 5460
Published: Aug. 23, 2022
Abstract
The
silica
gel
promoted
or
solvent-promoted
protonative
intramolecular
cyclization
of
ynamides
containing
an
o-(methylthio)aryl
group
resulted
in
the
one-pot
formation
biologically
important
benzo[b]thiophenes.
Compared
with
ynamide
activation
methods
that
use
strong
Brønsted
acids
expensive
transition
metals,
this
protocol
is
mild
and
economical.
Due
to
these
merits,
various
functionalized
2-amidobenzo[b]thiophenes
were
furnished
a
convenient
way.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(11), P. 2495 - 2500
Published: April 13, 2024
Abstract
Inexpensive
cobalt‐catalyzed,
pivalic
acid‐assisted
oxidative
C−H
functionalization
of
benzimidates
or
NH‐benzaldimines
with
ynamides
is
presented,
providing
an
access
to
3‐aminoisoquinoline
derivatives.
The
procedure
compatible
various
substrates
featuring
alkyl,
alkoxy,
acyl
halogen
as
substituents,
heteroaryl
structures,
and
diverse
ynamides.
reaction
has
been
scaled
up,
subsequent
transformation
the
yielded
products.
Control
experiments
mechanistic
investigations
corroborate
regioselectivity
this
conversion,
positioning
amine
group
proximal
nitrogen
atom
in
isoquinolines.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(24), P. 15939 - 15947
Published: Nov. 28, 2023
A
regiodivergent
oxidative
cyclization
of
ynamide-tethered
benzaldehydes
has
been
achieved
using
an
organocatalytic
approach
based
on
NHC/base.
The
method
enables
the
efficient
synthesis
aminolactones
with
high
regioselectivity,
including
formation
5-exo
products
through
umpolung
β-addition
ynamides.
reaction
involves
NHC-catalyzed
aerobic
oxidation
benzaldehyde
moiety
followed
by
toward
ynamide.
Computational
and
experimental
studies
have
shed
light
significance
proton
dissociation
from
in
situ
generated
carboxylic
acid
determining
regioselectivity
reaction.
synthetic
versatility
value
obtained
this
are
also
highlighted.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(38), P. 6914 - 6918
Published: Sept. 20, 2022
A
trans-iodo(III)etherification
reaction
of
ynamides
with
benziodoxole
triflate
and
alcohols
is
reported.
Despite
the
sensitivity
enamides
toward
Brønsted
acid,
could
be
successfully
performed
under
carefully
controlled
conditions
to
afford
β-alkoxy-β-amido
vinylbenziodoxoles
in
moderate
good
yields.
The
products
subjected
a
sequence
cross-coupling
via
C-I(III)
bond
cleavage
electrophilic
halogenation
resulting
α-alkoxyenamides,
allowing
for
preparation
densely
functionalized
esters.
Synthesis,
Journal Year:
2023,
Volume and Issue:
55(19), P. 3073 - 3089
Published: June 21, 2023
Abstract
Halogenative
annulation
of
alkyne-tethered
N-
and
O-containing
arenes
represents
a
general
strategy
for
the
construction
various
halogenated
O-heterocycles.
The
methods
employed
are
useful
in
producing
valuable
synthetic
building
blocks
carrying
C(sp2)–halide
functional
groups,
which
handles,
especially
cross-coupling
reactions
myriad
other
transformations.
When
alkyne
is
tethered
to
heteroatom
via
an
aromatic
ring,
reaction
gives
rise
aryl-fused
heterocycles.
In
this
Short
Review,
past
present
halogenative
construct
O-heterocycles
examined,
with
focus
on
more
recent
technologies
roles
participating
halogenating
agents.
Additionally,
future
directions
age-old,
but
still
very
useful,
considered.
1
Introduction
2
Synthesis
Aryl-Fused
Halogenated
N-Heterocycles
2.1
5-Membered
2.2
6-Membered
2.3
7-Membered
3
O-Heterocycles
3.1
3.2
3.3
4
Conclusion
Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
11(8)
Published: June 9, 2022
Abstract
Ynamides
are
recognized
as
electron‐rich
π‐components
and
show
high
reactivity
toward
electrophiles
such
iodonium
salts.
Here
we
report
the
iodocyclization
of
ene‐ynamides
arene‐ynamides
leading
to
naphthalenes
phenanthrenes.
We
found
these
reactions
were
completed
within
3
seconds
by
using
I(coll)
2
PF
6
an
reagent,
cyclized
products
obtained
in
good
yields.
To
best
our
knowledge,
this
method
is
most
rapid
synthesis
known
date
polycyclic
aromatic
compounds.
Organic & Biomolecular Chemistry,
Journal Year:
2021,
Volume and Issue:
19(40), P. 8746 - 8753
Published: Jan. 1, 2021
A
PhI(OAc)2-mediated
trifluoromethylthiolation/oxidative
cyclization
of
ynamides
with
the
Shen
reagent
has
been
established
herein,
providing
a
facile
access
to
CF3S-substituted
oxazolidine-2,4-diones
bearing
quaternary
carbon
center
in
38-85%
yields
chemoselectivities
up
99/1.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(20), P. 4096 - 4107
Published: Jan. 1, 2024
Electrophile-promoted
cyclizations
of
functionalized
alkynes
offer
a
useful
tool
for
constructing
halogen-substituted
heterocycles
primed
further
derivatization.
Preinstallation
an
iodo-substituent
at
the
alkyne
prior
to
iodo-cyclization
opens
access
