ARKIVOC,
Год журнала:
2022,
Номер
2022(9), С. 40 - 50
Опубликована: Авг. 25, 2022
An
efficient
and
practical
method
for
the
synthesis
of
aromatic
esters
from
aryl
acyl
peroxides
phenols,
naphthols
or
3-hydroxypyridines
at
room
temperature
was
realized.A
series
were
synthesized
in
high
yields
with
excellent
selectivity
presence
1,4-diaza[2.2.2]bicyclooctane
(DABCO)
without
use
transition-metals
acid
catalysts.This
operation
is
simple,
it
has
a
good
compatibility
various
functional
groups,
especially
heterocyclic
pyridine
substrates.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(16), С. 11562 - 11580
Опубликована: Июль 27, 2023
Diverse
functionalized
dihydrobenzofuran
spiro-indanedione-oxindole
scaffolds
were
conveniently
synthesized
by
base-promoted
cyclization
reaction
of
Morita-Baylis-Hillman
(MBH)
carbonates
isatins
and
2-(o-hydroxybenzylidene)-1,3-indanediones.
The
two
diastereomeric
dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines]
could
be
selectively
using
DABCO
or
DMAP
as
a
base
promoter.
More
importantly,
facilitated
the
annulation
MBH
formates
2-(o-hydroxybenzylidene)-1,3-indanediones
selectively,
resulting
in
spiro[cyclopropa[c]chromene-1,2'-indene]-1',3'-diones
dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines].
Additionally,
similar
with
maleimides
afforded
dispiro[indene-2,5'-benzofuro[2',3':1,5]cyclopenta[1,2-c]pyrrole-4',3″'-indolines]
high
yields
diastereoselectivity.
Organic Letters,
Год журнала:
2022,
Номер
24(42), С. 7790 - 7795
Опубликована: Окт. 14, 2022
We
have
developed
an
efficient
protocol
for
the
construction
of
polycyclic
dihydrobenzofuran
spirooxindole
scaffolds
via
base
promoted
cascade
annulation
Morita-Baylis-Hillman
(MBH)
carbonates
isatins
with
ortho-hydroxychalcones
or
ortho-hydroxy-β-nitrostyrenes.
The
complex
compounds
were
conveniently
synthesized
in
satisfactory
yields
and
high
diastereoselectivity.
This
provides
a
swift
convenient
approach
assembly
diverse
highly
functionalized
spirooxindoles
also
features
broad
substrate
scope,
molecular
convergence,
excellent
atomic
economy.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
10(2), С. 540 - 547
Опубликована: Дек. 10, 2022
An
efficient
synthetic
protocol
for
the
selective
construction
of
spiro[indoline-3,5′-pyrrolo[3,4-
b
]azepines]
and
spiro[indoline-3,3′-pyrroles]
via
a
cycloaddition
reaction
α,β-unsaturated
aldimines
MBH
adducts
isatins
was
successfully
developed.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(9), С. 5440 - 5456
Опубликована: Апрель 3, 2023
p-TsOH-catalyzed
cycloaddition
of
various
3-vinylindoles
and
(indol-2-yl)diphenylmethanols
in
acetonitrile
gave
the
functionalized
cyclopenta[b]indoles
good
yields
with
high
diastereoselectivity
via
[3
+
2]
reaction.
More
importantly,
FeCl3-catalyzed
annulation
reaction
afforded
unexpected
cyclohepta[1,2-b:4,5-b']diindoles
satisfactory
yields,
which
a
formal
[4
3]
an
unprecedented
C3/C2
carbocation
rearrangement
were
first
confirmed
by
determination
single-crystal
structure.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(35), С. 7099 - 7104
Опубликована: Янв. 1, 2022
An
efficient
method
to
construct
unique
spiro[indoline-3,4′-pyrrolo[3,4-
b
]pyridines]
was
successfully
developed
via
a
DABCO
promoted
formal
[3
+
3]
cycloaddition
reaction
of
MBH
carbonates
isatins
with
β-enamino
maleimides
under
mild
conditions.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(24), С. 17181 - 17196
Опубликована: Ноя. 28, 2023
A
convenient
synthetic
protocol
for
regioselective
and
diastereoselective
construction
of
complex
dispiro-indanone-fluorenone-oxindole
motifs
was
developed
by
the
base-promoted
annulation
reaction
bindone
MBH
carbonates
isatins
adjusting
conditions.
DABCO
promoted
in
DCM
at
room
temperature,
affording
dispiro[indene-2,4′-fluorene-1′,3″-indoline]
derivatives
good
yields
with
high
diastereoselectivity.
Triethylamine
two
molecular
1,3-indanediones
esters
ethanol
elevated
temperature
selectively
gave
dispiro[indene-2,4′-fluorene-3′,3″-indolines]
moderate
yields.
However,
triethylamine
excess
refluxing
ethanol,
Z-isomer
as
major
product
E-isomer
minor
product.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(24), С. 4964 - 4969
Опубликована: Янв. 1, 2022
Base
promoted
domino
reaction
of
bindone
([1,2′-biindenylidene]-1′,3,3′-trione)
with
common
1,3-dipolarophiles
showed
interesting
molecular
diversities.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(29), С. 6028 - 6033
Опубликована: Янв. 1, 2023
The
base
promoted
tandem
annulation
reaction
of
activated
cyclic
1,3-dipolarophiles
such
as
2-arylidene-1,3-indanediones,
2-(o-hydroxybenzylidene)-1,3-indanediones
and
3-methyleneoxindoles
with
functionalized
furo[2,3-d]pyrimidine-2,4-diones
was
systematically
investigated.
This
provided
efficient
synthetic
protocols
for
complex
dispiro/dispiro
fused
tricyclic
compounds
including
dispiro[indene-2,3'-cyclopentane-1',5''-pyrimidines],
dispiro[indoline-3,3'-cyclopentane-1',5''-pyrimidines]
spiro[cyclopenta[c]indeno[1,2-b]chromene-3,5'-pyrimidines]
in
good
yields
high
diastereoselectivity.
believed
to
proceed
via
sequential
ring-opening
the
furyl
ring,
formal
[3
+
2]
cycloaddition
o-hydroxyphenyl
group.
