Beilstein Journal of Organic Chemistry,
Год журнала:
2022,
Номер
18, С. 796 - 808
Опубликована: Июль 7, 2022
In
the
presence
of
copper
sulfate,
three-
or
four-component
reactions
2-methylindole,
aromatic
aldehydes
and
various
cyclic
dienophiles
in
refluxing
toluene
afforded
diverse
spirotetrahydrocarbazoles.
This
reaction
is
an
important
development
Levy
by
using
2-methylindole
to
replace
ethyl
indole-2-acetate
successfully
provides
facile
access
polysubstituted
spiro[carbazole-3,3'-indolines],
spiro[carbazole-2,3'-indolines],
spiro[carbazole-3,5'-pyrimidines]
spiro[carbazole-3,1'-cycloalkanes]
satisfactory
yields
with
high
diastereoselectivity.
iScience,
Год журнала:
2022,
Номер
25(9), С. 105005 - 105005
Опубликована: Авг. 28, 2022
One-pot
synthesis
is
an
active
topic
in
organic
chemistry
due
to
its
intrinsic
advantages
of
simple
operation,
high
mass
efficiency,
low
cost,
and
less
amount
waste
disposal.
Among
three
kinds
one-pot
syntheses,
1)
cascade
reactions,
2)
multicomponent
reactions
(MCRs),
3)
stepwise
(OPSS),
OPSS
could
be
more
flexible
practical
since
it
carried
out
stepwisely
have
variable
reaction
conditions
for
different
steps.
This
perspective
article
uses
selected
examples
highlight
the
recent
development
involving
cyclization,
cycloaddition,
rearrangement,
catalytic
heterocyclic
scaffolds,
asymmetric
molecules,
natural
products,
bioactive
compounds.
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.
Green Synthesis and Catalysis,
Год журнала:
2021,
Номер
3(1), С. 53 - 58
Опубликована: Окт. 22, 2021
A
new
DBU-catalyzed
formal
[4
+
2]
cycloaddition
between
ortho-hydroxyphenyl-substituted
para-quinone
methides
and
electron-deficient
dienophiles
including
3-methyleneoxindoles
2-aryldeneindene-1,3-diones
was
established.
wide
range
of
functionalized
spiro[chromane-3,3′-indolines]
spiro[chromane-3,2′-indenes]
were
successfully
synthesized
in
good
yields
with
high
diastereoselectivity.
The
features
the
reaction
included
readily
available
substrates,
mild
conditions,
convenient
methodology
functional
group
tolerance.
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:
2021,
Номер
86(21), С. 14705 - 14719
Опубликована: Окт. 18, 2021
A
DABCO-promoted
annulation
reaction
of
bindone
([1,2′-biindenylidene]-1′,3,3′-trione)
and
3-methyleneoxindoles
showed
very
interesting
molecular
diversity
under
different
conditions.
The
base-promoted
3-phenacylideneoxindoles
in
DCM
at
room
temperature
afforded
spiro[indeno[1,2-a]fluorene-5,3′-indoline]
derivatives
good
yields
with
high
diastereoselectivity.
However,
the
similar
2-(2-oxoindolin-3-ylidene)
acetates
resulted
Z/E-isomeric
spiro[indeno[1,2-a]fluorene-5,3′-indolines]
diastereomeric
ratios
2:1
to
10:1.
On
other
hand,
acetonitrile
temperatures
selectively
gave
spiro[benzo[5,6]pentaleno[1,6a-b]naphthalene-7,3′-indoline]
complex
dispiro[indoline-3,6′-[4b,6a]ethanoindeno[1,2-a]fluorene-14′,3″-indolines]
satisfactory
yields.
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.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(14), С. 9263 - 9279
Опубликована: Июль 1, 2021
p-TsOH
catalyzed
Diels–Alder
reaction
of
2-(1-alkylindol-3-yl)naphthalene-1,4-diones
and
3-phenacylideneoxindoles
showed
fascinating
diastereoselectivity.
The
with
the
hydrated
afforded
trans-isomers
dihydrospiro[indoline-3,6′-naphtho[2,3-c]carbazoles]
as
major
products.
Alternatively,
anhydrous
under
a
Dean
Stark
apparatus
predominately
gave
cis-isomer
dihydrospiro[indoline-3,6′-naphtho[2,3-c]carbazoles].
On
other
hand,
similar
2-(indol-3-yl)naphthalene-1,4-diones
3-arylideneindolin-2-ones
cis/trans-isomers
Additionally,
2-arylidene-1,3-indanediones
expected
spiro[indene-2,6′-naphtho[2,3-c]carbazoles]
in
satisfactory
yields.
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.
