Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(6)
Published: April 26, 2023
Abstract
A
NaH‐promoted
domino
reaction
between
azadiene
bearing
an
indene
moiety
with
Nazarov
reagent
was
developed.
variety
of
spiro[4.5]decane
derivatives
were
obtained
via
[4+2]
cycloaddition
good
yields
and
high
diastereoselectivity.
The
strategy
benefited
from
mild
conditions
very
broad
substrate
scope.
Furthermore,
a
gram‐scale
experiment
transformation
the
product
carried
out.
Lastly,
density
functional
theory
(DFT)
calculations
have
been
performed
to
verify
proposed
mechanism
analyze
observed
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(21), P. 15041 - 15059
Published: Oct. 19, 2023
A
facile
and
efficient
synthesis
of
structurally
diversified
2-pyridones
is
demonstrated
using
the
[4
+
2]
annulation
in
situ
generated
azadienes
from
N-propargylamines
active
methylene
compounds.
The
reaction
promoted
by
an
inorganic
base
giving
moderate
to
good
yields.
developed
methodology
applicable
for
direct
formal
various
bioactive
molecules.
synthetic
utility
protocol
was
also
illustrated
late-stage
functionalization
products.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(35), P. 7106 - 7114
Published: Jan. 1, 2023
An
efficient
visible-light-induced
Staudinger
[2
+
2]
annulation
reaction
between
α-diazo
ketones
and
dibenzo[b,f][1,4]oxazepine/thiazepine-imines
under
catalyst-free
conditions
has
been
developed.
This
protocol
provides
a
facile
method
to
synthesize
tetracyclic
dibenzo[b,f][1,4]oxazepine/thiazepine-fused
β-lactams
bearing
quaternary
carbon
center
with
broad
substrate
scope
high
efficiency
(37
examples,
up
>99%
yield).
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(47), P. 8698 - 8702
Published: Nov. 18, 2022
Palladium(0)-catalyzed
reactions
between
allenamides
3
or
4
and
aryl
iodides/bromides
5/6
provide
an
easy
access
to
δ-carbolines
1
benzofuro[3,2-b]pyridines
2.
The
reaction
constitutes
a
fast
intermolecular
assembly
that
takes
place
in
one
pot,
the
choice
of
phosphine
ligand
is
critical
for
success.
A
plausible
mechanism
proposed.
amenable
synthesis
bis-heteroannulated
products.
Synthesis,
Journal Year:
2022,
Volume and Issue:
55(10), P. 1561 - 1569
Published: Dec. 8, 2022
Abstract
An
array
of
spiro[benzofuran-2,3′-pyrazol]-3-imines
with
diverse
functional
groups
were
readily
assembled
from
aurone-derived
azadienes
and
in-situ
generated
nitrilimines
under
mild
conditions.
The
transformation
was
performed
in
a
regio-
diastereoselective
fashion,
which
synergetic
[2+3]
cycloaddition
pathway
likely
involved.
This
novel
methodology
has
extended
the
synthetic
application
as
kind
two-atom
synthon.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
21(5), P. 1033 - 1037
Published: Dec. 29, 2022
A
highly
efficient
metal-free
selective
1,4-addition
reaction
of
difluoroenoxysilanes
to
chromones
was
developed
using
the
low-cost
and
readily
available
HOTf
as
catalyst,
which
is
a
facile
straightforward
method
access
valuable
C2-difluoroalkylated
chroman-4-one
derivatives.
Interestingly,
products
could
be
converted
difluorinated
bioisostere
natural
product
(S)-2,6-dimethylchroman-4-one
benzo-seven-membered
heterocycle
via
Schmidt
rearrangement
reaction.
In
addition,
in
vitro
anti-proliferative
activities
these
synthesized
derivatives
against
human
colon
carcinoma
cells
(HCT116)
revealed
that
compound
3g
exhibited
potent
inhibitory
effect
on
HCT116
cancer
with
an
IC50
value
6.37
μM,
representing
novel
lead
for
further
structural
optimization
biological
evaluation.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
21(5), P. 925 - 929
Published: Dec. 28, 2022
Despite
many
studies
on
benzofuran-derived
azadiene
being
reported,
multi-component
have
scarcely
been
reported
this
heterocyclic
skeleton.
The
first
cascade
three-component
acyloxylation
of
diazos
with
acids
and
azadienes
has
under
mild
conditions.
reaction
is
applicable
to
various
(A/A)
diazo
compounds,
generating
diverse
complex
benzofuran
derivatives.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(23), P. 5863 - 5869
Published: Jan. 1, 2023
This
work
disclosed
an
unprecedented
carbodiimide
anion
participated
cascade
[4
+
2]
annulation/aromatization
reaction,
affording
efficient
method
for
synthesizing
2-aminopyrimidines.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(24), P. 4550 - 4555
Published: Nov. 14, 2023
Abstract
The
etherification
and
amination
of
difluoroenol
silyl
ethers
with
benzoquinones
quinonediimines
were
achieved
by
using
hexafluoroisopropanol
(HFIP)
as
the
solvent.
This
1,6‐addition
reaction
could
construct
difluorooxymethyl
difluoroaminomethyl
compounds
under
metal‐free
conditions.
It
is
preliminarily
speculated
that
took
place
through
a
single
electron
transfer
(SET)
process.
European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
2022(35)
Published: Aug. 5, 2022
Abstract
The
KI/TBHP
(
tert
‐butyl
hydroperoxide)
promoted
[3+2]
annulation
between
dibenzo[
b,f
][1,4]oxazepine‐imines
(DBO‐Imines)
and
N
‐tosylhydrazones
under
mild
conditions
has
been
developed,
affording
a
direct
high
atom‐economical
preparation
for
tetracyclic
1,2,4‐triazoline‐fused
][1,4]oxazepines
(DBOs)
in
good
to
excellent
yields.
This
procedure
could
tolerate
wide
range
of
functional
groups
also
be
conveniently
conducted
on
gram‐scale
reaction,
even
one‐pot
fashion.
produced
DBOs
easily
converted
into
biologically
interesting
1,2,4‐triazolo‐fused
the
action
NBS
‐bromosuccinimide).
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(11)
Published: Jan. 13, 2023
Abstract
A
metal‐free
1,4‐allylation
of
azadienes
with
allyltrimethylsilanes
catalyzed
by
B(C
6
F
5
)
3
has
been
developed.
The
high
Lewis
acidity,
good
thermal
stability,
and
hydrolytic
stability
the
catalyst
make
this
reaction
efficient
operationally
simple.
In
contrast
to
previously
reported
1,2‐allylation
α,β‐unsaturated
imines,
is
described
here
for
first
time.
Benzofuran‐,
indene‐,
dihydronaphthalene‐,
chromene‐,
benzothiophene‐based
allyl
arylmethanes
have
obtained
in
up
95
%
yield.
