Synthesis spiro and fused chromenes via [4 + 2] cycloaddition of salicyl N-tosylimines and cyclic dienophiles
Journal of Molecular Structure,
Год журнала:
2024,
Номер
1304, С. 137684 - 137684
Опубликована: Фев. 4, 2024
Язык: Английский
Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction
Beilstein Journal of Organic Chemistry,
Год журнала:
2024,
Номер
20, С. 1436 - 1443
Опубликована: Июнь 28, 2024
An
efficient
protocol
for
the
synthesis
of
polyfunctionalized
tetrahydrocyclopenta[4,5]pyrrolo[2,3-
b
]pyridine-3,4b,5,6,7(1
H
)-pentacarboxylates
was
developed
by
a
three-component
reaction.
In
absence
any
catalyst,
reaction
alkyl
isocyanides,
dialkyl
but-2-ynedioates
and
5,6-unsubstituted
1,4-dihydropyridines
in
refluxing
acetonitrile
afforded
high
yields
with
diastereoselectivity.
The
finished
situ
generation
activated
5-(alkylimino)cyclopenta-1,3-dienes
from
addition
isocyanide
to
two
molecules
sequential
formal
[3
+
2]
cycloaddition
1,4-dihydropyridine.
Язык: Английский
Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(15), С. 10854 - 10866
Опубликована: Июль 12, 2024
A
convenient
synthetic
protocol
for
diverse
fused
chromenes
was
successfully
developed
by
a
three-component
reaction
of
alkyl
isocyanides,
dialkyl
but-2-ynedioates,
and
various
cyclic
1,3-dipolarophiles
containing
Язык: Английский
Construction of Spiro[indoline‐3,2′‐pyrrolo[2,1‐a]Isoquinoline] and Spiro[indoline‐3,2′‐pyrrolo[1,2‐a]Quinoline] via Isocyanide‐Based Three‐Component Reaction
ChemistrySelect,
Год журнала:
2025,
Номер
10(4)
Опубликована: Янв. 1, 2025
Abstract
A
convenient
synthetic
protocol
for
novel
spiro[indoline‐3,2′‐pyrrolo[2,1‐
a
]isoquinoline]
and
spiro[indoline‐3,2′‐pyrrolo[1,2‐
]quinoline]
motifs
was
successfully
developed
by
three‐component
reaction
of
isoquinoline
(quinoline),
cyclohexyl
isocyanide,
isatylidene
malononitriles.
In
the
absence
any
catalyst,
isoquinoline,
malononitriles
in
refluxing
dichloromethane
gave
functionalized
]isoquinolines]
good
yields
with
high
diastereoselectivity.
However,
similar
quinoline
afforded
]quinolines]
about
2:1
Язык: Английский
Diastereoselective Assembly of Dispiro-cyclopentene-linked Bisoxindoles via Annulation Involving Isatylidene Malononitriles and Benzylamines
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
Highly
diastereoselective
construction
of
the
dispiro-bisoxindole
skeleton
by
forming
5
new
bonds
and
two
rings.
Язык: Английский
Synthetic Protocol for Pyrido[2,3-c]pyridazine and Pyrido[3,2-e][1,2]oxazine Scaffolds via a [4 + 2] Cycloaddition Reaction
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 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.
Язык: Английский
Construction of Unique Spiro[dibenzo[a,f]azulene-6,2′-indenes] via Unprecedented Annulation of ortho-C–H Bond of Benzylidene Group
Yu‐Wei He,
Wei-Qing Ma,
Ying Han
и другие.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(21), С. 14911 - 14927
Опубликована: Окт. 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.
Язык: Английский
Iodine promoted annulation reaction for selective construction of Spiro[indene-2,1′-pyrido[4,3-b]indole] and Benzo[5,6]pyrrolo[3′,2': 3,4]cyclohepta[1,2-b]indole
Lingyun Zhu,
Jing Sun,
Dan Liu
и другие.
Tetrahedron,
Год журнала:
2024,
Номер
159, С. 134026 - 134026
Опубликована: Май 9, 2024
Язык: Английский
Construction of diverse spirooxindoles via a domino reaction of arylamines, but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones
Lingyun Zhu,
Jing Sun,
Dan Liu
и другие.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(47), С. 9392 - 9397
Опубликована: Янв. 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.
Язык: Английский