Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 21, 2024
Abstract
A
highly
efficient
cascade
aza‐MIRC
(Michael
Induced
Ring
Closure)
reaction
between
trifluoromethylpyrazole
(TFPZ)‐derived
oxadienes
and
a
‐bromohydroxamates
has
been
developed
for
the
construction
of
1,4‐oxazepinone
derivatives.
The
proceeds
smoothly
under
mild
conditions
via
Aza‐Michael
addition/intramolecular
S
N
2
sequence,
features
broad
substrate
scope,
transition‐metal
free,
operational
simplicity
etc.
utility
versatile
protocol
was
also
demonstrated
by
gram‐scale
valuable
synthetic
transformations.
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.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(22), С. 15805 - 15816
Опубликована: Окт. 31, 2023
An
Et3N-catalyzed
cascade
[3
+
2]-annulation
of
β-oxo-acrylamides
with
cyclic
N-sulfonyl
ketimines
or
sulfamate-derived
imines
is
developed
under
mild
reaction
conditions,
which
provides
a
concise
and
efficient
route
to
access
valuable
sultam-
sulfamidate-fused
imidazolidinone
derivatives
in
good
excellent
yields
(80–95%
yields)
diastereoselectivities
(>20:1
drs).
The
current
protocol
features
atom
economy,
transition-metal-free
process,
broad
functional
group
tolerance.
Moreover,
the
asymmetric
variant
2]-cycloaddition
was
achieved
presence
diphenylethanediamine
quinine-based
bifunctional
squaramide
organocatalysts
C-1
C-11,
giving
corresponding
chiral
polycyclic
imidazolidinones
68–90%
25–94%
ees
>20:1
drs
all
cases.
Chemical Communications,
Год журнала:
2020,
Номер
56(90), С. 14079 - 14082
Опубликована: Янв. 1, 2020
A
Cs2CO3-mediated
formal
[4+3]
cycloaddition
involving
benzofuran-derived
azadienes
(BDAs)
and
α-bromohydroxamates
to
afford
benzofuran-fused
1,4-diazepinones
is
established.
This
the
first
example
of
using
BDAs
for
construction
seven-membered
dinitrogen-fused
heterocycles.
strategy
not
only
enriches
chemistry
but
also
provides
an
interesting
class
bioisosteres
1,4-benzodiazepine.
Organic Letters,
Год журнала:
2022,
Номер
24(51), С. 9442 - 9446
Опубликована: Дек. 20, 2022
We
herein
designed
and
synthesized
allenyl
benzoxazinones
of
a
novel
type,
which
were
then
involved
in
Pd-catalyzed
asymmetric
cascade
intramolecular
cyclization/intermolecular
Michael
addition
reaction
with
1-azadienes.
A
broad
range
chiral
C2-functionalized
quinoline
derivatives
afforded
moderate
to
good
yields
(up
93%)
high
enantioselectivities
93%
ee)
this
reaction.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(12), С. 8158 - 8169
Опубликована: Июнь 8, 2022
The
additive-free
[3
+
2]
annulation
from
isatins,
amino
acids
with
2-styrylbenzoxazoles,
was
described,
providing
a
series
of
functional
and
structurally
complex
3,3'-pyrrolidinyl-spirooxindole
derivatives
containing
four
contiguous
two
quaternary
stereogenic
centers
in
high
yields
(up
to
95%)
excellent
diastereoselectivities
>25:1
dr).
Interestingly,
the
reaction
exhibits
switchable
regioselectivity
depending
on
substrate
acids.
With
proline
or
thioproline
as
substrate,
afforded
α-regioselective
spirooxindole
skeletons.
In
contrast,
when
piperidine
acid
is
provided
γ-regioselective
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
21(11), С. 2295 - 2300
Опубликована: Ноя. 17, 2022
Lewis
base-catalyzed
cascade
nucleophilic/aza-Michael
addition
reaction
of
N-alkoxy
β-oxo-acrylamides
with
isocyanates
has
been
developed
to
afford
various
highly
functionalized
hydantoin
derivatives
in
80-98%
yields
under
mild
conditions.
The
intriguing
features
this
method
include
metal-free
conditions,
low
catalyst
loading,
broad
substrate
scope
and
short
time.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(13), С. 3336 - 3347
Опубликована: Май 6, 2021
Abstract
A
Brønsted
base‐catalyzed
tandem
[2+4]
annulation/tautomerization/aromatization
reaction
of
α‐alkylidene
succinimides
with
5‐alkenyl
thiazolones
has
been
developed
for
synthesis
functionalized
thiazolo
pyrones
under
mild
conditions.
The
prepared
show
fluorescent
properties.
magnified
image
Synlett,
Год журнала:
2021,
Номер
32(10), С. 981 - 986
Опубликована: Май 19, 2021
Abstract
A
Pd-catalyzed
oxa-(4+4)-cycloaddition
between
1-azadienes
and
(2-hydroxymethyl)allyl
carbonates
is
described.
Aurone-derived
azadienes
furnished
polycyclic
1,5-oxazocines
in
good
yields.
Interestingly,
linear
have
also
been
involved
yielded
monocyclic
heterocycles
with
complete
regioselectivity.
DFT
calculations
were
carried
out
to
gain
insight
on
this
observation.
European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(47)
Опубликована: Окт. 10, 2022
Abstract
Aza‐oxyallyl
cations,
as
proposed
by
Sheehan
in
the
1960s
have
garnered
significant
attention
among
synthetic
organic
community,
owing
to
their
diverse
reactivity
profile
for
constructing
N‐scaffolds
of
biological
interest.
During
its
initial
growth,
aza‐oxyallyl
cations
were
used
effectively
a
3‐unit
synthon
1,3
dipoles
create
N‐heterocycles
via
cycloaddition
reactions,
wherein
cation
served
electrophilic
counterpart.
Recently,
new
variations
been
reported,
including
usage
1,4
dipole
domino
and
unique
alkylating
ability
heteroatoms.
This
review
article
provides
an
update
recent
developments
this
area
prevailing
mechanistic
insight.
