Organic & Biomolecular Chemistry,
Journal Year:
2016,
Volume and Issue:
14(30), P. 7136 - 7149
Published: Jan. 1, 2016
Pyrroles
are
important
synthetic
targets
as
a
result
of
their
occurrence
in
numerous
biologically
active
molecules,
roles
diverse
living
processes,
and
utility
versatile
intermediates.
As
consequence,
efforts
focused
on
the
development
concise
efficient
methods
for
construction
pyrroles.
Compared
with
other
transition
metals,
group
1B
metals
(Cu,
Ag
Au)
probably
more
widely
used
synthesis
pyrroles
organic
chemistry.
Considering
importance
both
topics
synthesis,
here
we
summarize
recent
achievements
catalyzed
by
monometallic
systems
which
belong
to
Au).
The Journal of Organic Chemistry,
Journal Year:
2018,
Volume and Issue:
83(4), P. 2104 - 2113
Published: Jan. 22, 2018
The
facile
copper-catalyzed
synthesis
of
polysubstituted
pyrroles
from
aldehydes,
amines,
and
β-nitroalkenes
is
reported.
Remarkably,
the
use
α-methyl-substituted
aldehydes
provides
efficient
access
to
a
series
tetra-
pentasubstituted
via
an
overwhelming
1,2-phenyl/alkyl
migration.
present
methodology
also
accessible
non
α-substituted
yielding
corresponding
trisubstituted
pyrroles.
On
contrary,
ketones,
in
place
does
not
promote
organic
transformation,
signifying
necessity
aldehydes.
reaction
proceeds
under
mild
catalytic
conditions
with
low
catalyst
loading
(0.3-1
mol
%),
broad
scope,
very
good
functional-group
tolerance,
high
yields
can
be
easily
scaled
up
more
than
3
mmol
product,
thus
highlighting
useful
synthetic
application
protocol.
Based
on
formal
kinetic
studies,
possible
radical
pathway
proposed
that
involves
formation
allylic
nitrogen
intermediate,
which
turn
reacts
nitroalkene
yield
desired
pyrrole
framework
1,2-phenyl
or
alkyl
Chemical Communications,
Journal Year:
2015,
Volume and Issue:
51(53), P. 10726 - 10729
Published: Jan. 1, 2015
An
efficient
and
unprecedented
domino
reaction
of
methyleneindolinones
andN-tosyloxycarbamates
was
realized
to
construct
bispirooxindoles
spirooxindole
aziridines.
ARKIVOC,
Journal Year:
2017,
Volume and Issue:
2018(1), P. 50 - 113
Published: Nov. 12, 2017
The
inherent
reactivity
of
the
aziridine
ring
due
to
ring-strain
makes
it
valuable
building
blocks
for
synthesis
other
heterocyclic
motifs
biological
relevance.Of
particular
significance
is
generation
azomethine
ylides
from
them
and
cycloaddition
with
alkenes,
alkynes,
heterocumulenes.The
undergoes
opening
followed
by
cyclization
a
variety
reagents
either
in
presence
catalyst
or
without
any
catalyst.This
review
article
discusses
recent
applications
aziridines
syntheses
four-to
seven-membered
heterocycles
relevance
such
as
azetidines,
2-azetidinones,
pyrroles,
imidazoles,
oxazoles,
thiazoles,
piperidines,
pyrazines,
pyrimidines,
benzoxazines,
morpholines,
azepanes,
benzodiazepines,
benzoxazepines,
benzothiazepines.
The Journal of Organic Chemistry,
Journal Year:
2019,
Volume and Issue:
84(18), P. 11581 - 11595
Published: Aug. 21, 2019
A
new
one-pot,
transition-metal,
acid/base-free
domino
process
is
developed
for
the
regioselective
synthesis
of
1,2,4-trisubstituted
pyrroles.
The
involves
1,3-dipolar
cycloaddition
unsymmetrical
azomethine
ylide
resulting
from
thermal
C-C
bond
cleavage
unactivated
aziridines
with
β-bromo-β-nitrostyrene,
followed
by
a
cascade
elimination
and
aromatization
reaction
sequence
to
preferentially
furnish
pyrroles
instead
expected
1,2,3-trisubstituted
pyrroles,
in
good
excellent
yields.
Further,
application
methodology
formal
ningalin
B
delineated.
Synthesis,
Journal Year:
2021,
Volume and Issue:
54(04), P. 910 - 924
Published: July 9, 2021
Abstract
Cycloaddition
reactions
have
emerged
as
rapid
and
powerful
methods
for
constructing
heterocycles
carbocycles.
[3+2]
Cycloadditions
of
nitroalkenes
with
various
1,3-dipoles
been
an
interesting
research
area
many
organic
chemists.
This
review
outlines
the
synthesis
N-substituted
NH-1,2,3-triazoles
along
other
five-membered
N-heterocycles
through
cycloaddition
nitroalkenes.
1
Introduction
2
Synthesis
1,2,3-Triazoles
2.1
NH-1,2,3-Triazoles
2.2
N-Substituted
3
Pyrrolidines
Pyrroles
4
Pyrazoles
5
Conclusion
Synthesis,
Journal Year:
2017,
Volume and Issue:
49(23), P. 5093 - 5104
Published: Sept. 6, 2017
This
review
highlights
recent
achievements
in
the
transformations
of
2-acylaziridines
toward
synthesis
cyclic
and
acyclic
nitrogen-containing
compounds.
The
influence
a
carbonyl
group
on
reaction
selectivity
is
discussed.
1
Introduction
2
Reactions
via
C–C
Bond
Cleavage
3
C–N
3.1
Starting
with
Aziridine
Ring
Opening
3.2
at
Carbonyl
Group
4
Conclusion
