ACS Omega,
Journal Year:
2023,
Volume and Issue:
9(1), P. 934 - 941
Published: Dec. 20, 2023
An
easy
and
simple
spiroannulation
of
the
Morita–Baylis–Hillman
adduct
isatin
derivatives
with
anthracene
was
achieved
in
moderate-to-good
yields
(37–75%).
The
spiroderivatives
synthesized
this
work
exhibited
green
fluorescence
properties.
reaction
occurred
metal-free
eco-friendly
K-10
clay-mediated
conditions.
final
products
have
multiple
structural
features
such
as
3-spirooxindole,
fluorophoric
anthracene,
phenanthracene,
phenalene,
perylene
cores.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 14, 2025
Here,
we
revealed
a
convenient
synthetic
protocol
for
unique
pyrido[2,3-c]pyridazine
and
pyrido[3,2-e][1,2]oxazine
scaffolds
with
excellent
regioselectvity
diastereoselectivity.
The
functionalized
pyrido[2,3-c]
pyridazines
were
successfully
synthesized
via
Cs2CO3-promoted
[4
+
2]
cycloaddition
reaction
of
α-halogenated
N-tosylhydrazones
or
N-acylhydrazones
5,6-unsubstituted
1,4-dihydropyridines
under
mild
conditions.
Additionally,
the
similar
base-promoted
α-chlorogenated
oximes
afforded
pyrido[3,2-e][1,2]oxazines
in
satisfactory
yields.
features
this
included
conditions,
broad
substrate
scopes,
high
functional
group
tolerance,
significant
atomic
economy.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(21), P. 14911 - 14927
Published: Oct. 23, 2023
The
domino
reaction
of
alkyl
and
aryl
isocyanides
with
two
molecules
2-arylidene-1,3-indanediones
in
acetonitrile
at
80
°C
resulted
unique
functionalized
spiro[dibenzo[a,f]azulene-6,2'-indenes]
good
yields,
which
the
acted
as
different
building
blocks
to
construct
polycyclic
system.
More
importantly,
unprecedented
anticipation
ortho-position
benzylidene
group
form
a
novel
dibenzo[a,f]azulene
ring
through
formal
[5
+
2]
cycloaddition
process
was
first
observed.
On
other
hand,
DABCO-promoted
afforded
spiro[cyclopenta[a]-indene-2,2'-indene]
derivatives.
ChemistrySelect,
Journal Year:
2023,
Volume and Issue:
8(39)
Published: Oct. 19, 2023
Abstract
DABCO
promoted
one‐pot
three‐component
reaction
of
aromatic
amines,
dialkyl
but‐2‐ynedioates
and
MBH
nitriles
isatins
selectively
afforded
two
diastereomeric
spiro[indoline‐3,4′‐pyridines]
in
comparable
yields.
On
the
other
hand,
cyclization
carbonates
DCM
at
room
temperature
gave
spiro[cyclopentane‐1,3′‐indoline]
derivatives,
while
chloroform
70
°C
resulted
unique
cyclopenta[
c
]quinolone
derivatives
with
ring‐opening
isatin
moiety.
A
plausible
mechanism
was
rationally
proposed
to
explain
formation
different
products.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(12)
Published: Feb. 21, 2024
Abstract
A
promising
and
useful
method
has
been
accomplished
for
regio‐
diastereoselective
synthesis
of
tetrahydro‐benzofuro[3,2‐
c
]chromenones
through
ceric(IV)
ammonium
nitrate
(CAN)
mediated
oxidative
coupling
cyclic/acyclic
1,3‐dicarbonyl
compounds
to
2‐aryl/heteroarylchromenes
followed
by
a
base
assisted
cyclization.
The
significant
features
the
encircle
easy
accessibility
starting
materials,
high
air
stability
low
toxicity
oxidant
CAN,
product
yield,
operationally
simple
eco‐friendly
reaction
conditions.
Trapping
radical
intermediate
with
scavenger
TEMPO
(detected
LC–MS)
from
mixture
proved
that
is
process.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 17, 2024
Abstract
The
diverse
functionalized
dihydrobenzofuran‐fused
spirocyclopentane‐1,2‐diindolin‐one
scaffolds
were
conveniently
synthesized
by
base
promoted
domino
cyclization
reaction
of
MBH
(Morita‐Baylis‐Hillmann)
carbonates
isatins
and
3‐(
o
‐hydroxybenzylidene)indolin‐2‐ones.
reactions
maleimides
formates
with
‐hydroxybenzylidene)indolin‐2‐ones
afforded
polycyclic
dispiro[indoline‐3,4′‐benzofuro[2′,3′:1,5]cyclopenta[1,2‐
c
]pyrrole‐5′,3′′‐indolines]
dispiro[indoline‐3,1′‐cyclopenta[
b
]benzofuran‐2′,3′′‐indolines]
in
good
yields
high
diastereoselectivity.
More
importantly,
DMAP
facilitated
annulation
nitriles
selectively
resulted
dispiro[indoline‐3,1′‐cyclopentane‐2′,3′′‐indolines],
while
Cs
2
CO
3
gave
relative
configurations
the
various
compounds
clearly
elucidated
determination
several
single
crystal
structures.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(47), P. 9392 - 9397
Published: Jan. 1, 2023
An
iodine-promoted
domino
reaction
of
arylamines/benzylamines,
dialkyl
but-2-ynedioates
and
3-hydroxy-3-(indol-3-yl)indolin-2-ones
showed
very
interesting
molecular
diversity.
The
in
acetonitrile
at
65
°C
the
presence
30%
mmol
I2
resulted
spiro[indoline-3,1'-pyrido[4,3-b]indoles]
satisfactory
yields.
When
anilines
without
para-substituents
were
used
reaction,
a
direct
substitution
hydroxyl
group
to
2-(phenylamino)maleate
para-position
aniline
gave
chain
products
good
Additionally,
similar
reactions
with
benzylamines
not
only
spiro[indoline-3,1'-pyrido[4,3-b]indoles],
but
also
afforded
spiro[indoline-3,1'-pyrano[4,3-b]indol]-2-ones
lower
A
plausible
annulation
mechanism
was
rationally
proposed
for
formation
different
kinds
polycyclic
compounds.
ChemistrySelect,
Journal Year:
2023,
Volume and Issue:
8(37)
Published: Oct. 2, 2023
Abstract
A
convenient
synthetic
protocol
for
the
construction
of
spiro[indoline‐3,3′‐quinoline]‐2,5′‐dione
motifs
was
successfully
developed
by
base
promoted
one‐pot
three‐component
reaction.
In
presence
piperidine,
reaction
ammonium
acetate,
aromatic
aldehydes
and
in
situ
generated
3‐isatyl
1,4‐dicarbonyl
compounds,
which
were
derived
from
mediated
addition
dimedone
to
3‐methyleneoxindoles,
resulted
two
diastereoisomers
derivatives
good
yields
with
diastereoselectivity.
The
stereochemistry
clearly
elucidated
isolation
diastereomers
determination
several
single
crystal
structures.
