We
present
a
Diversity
Oriented
Clicking
approach
to
synthesize
library
of
novel
clickable
N-substituted
2-aminothiazoles
which
serve
as
versatile
hubs
for
SuFEx
click
chemistry
diversification.
Leveraging
the
spring-loaded
reactivity
2-Substituted-Alkynyl-1-Sulfonyl
Fluoride
(SASF)
connectors,
transformation
is
simple
perform,
tolerant
wide
range
functionality,
and
regioselective
single
product.
Finally,
we
propose
detailed
stepwise
reaction
mechanism
that
supported
by
experimental
computational
analysis.
Abstract
Heterocycles
are
a
vital
class
of
compounds
in
numerous
fields,
including
drug
discovery,
agriculture,
and
materials
science.
Efficient
methods
for
the
synthesis
heterocycles
remain
critical
meeting
demands
these
industries.
Recent
advances
multicomponent
reactions
(MCRs)
utilizing
2‐aminobenzothiazole
(ABT)
have
shown
promising
results
formation
heterocycles.
The
versatility
this
context
has
enabled
rapid
efficient
construction
diverse
heterocyclic
structures.
Various
synthetic
methodologies
involving
discussed,
highlighting
its
importance
as
valuable
building
block
complex
potential
applications
discovery
material
science
also
explored.
Overall,
review
provides
comprehensive
overview
current
state
research
field
offers
insights
into
future
directions
area
study.
We
highlight
ABT
versatile
sustainable
starting
via
MCRs,
with
significant
implications
chemical
industry.
Molecules,
Год журнала:
2021,
Номер
27(1), С. 132 - 132
Опубликована: Дек. 27, 2021
In
this
review,
we
comprehensively
describe
catalyzed
multicomponent
reactions
(MCRs)
and
the
multiple
roles
of
catalysis
combined
with
key
parameters
to
perform
these
transformations.
Besides
improving
yields
shortening
reaction
times,
is
vital
achieving
greener
protocols
furthering
MCR
field
research.
Considering
that
MCRs
typically
have
two
or
more
possible
pathways
explain
transformation,
essential
for
selecting
a
route
avoiding
byproduct
formation.
Key
parameters,
such
as
temperature,
catalyst
amounts
reagent
quantities,
were
analyzed.
Solvent
effects,
which
are
likely
most
neglected
topic
in
MCRs,
well
their
catalysis,
critically
discussed.
Stereocontrolled
rarely
observed
without
presence
catalytic
system,
also
presented
discussed
review.
Perspectives
on
use
systems
improved
finally
presented.
Synthesis,
Год журнала:
2024,
Номер
56(16), С. 2445 - 2461
Опубликована: Янв. 8, 2024
Abstract
The
unique
reactivity
and
beneficial
features
of
the
5-aminotetrazole
synthon
(1H-tetrazol-5-amine)
have
made
it
a
versatile
effective
building
block
in
synthesis
heterocyclic
compounds.
In
addition,
several
drugs
containing
this
scaffold
with
wide
array
biological
properties
been
already
introduced.
Heterocyclic
structures
are
backbone
many
biologically
active
industrially
important
5-Aminotetrazole
is
one
favored
synthons
used
preparation
heterocycle-bearing
compounds,
especially
multicomponent
synthesis.
This
review
highlights
comprehensive
overview
emerging
applications
as
key
component
frameworks
through
reactions,
reported
between
2017
July
2023.
1
Introduction
2
3
Tetrazolopyrimidine
Compounds
4
Spiro
5
Miscellaneous
6
Conclusion
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(10), С. 1708 - 1715
Опубликована: Апрель 13, 2022
Abstract
An
enantioselective
chiral
phosphoric
acid
catalyzed
formal
[4+2]
cycloaddition
between
2‐benzothiazolimines
and
N
‐H‐1,3‐dienecarbamates
is
described.
A
divergence
in
reaction
pathways
was
observed
depending
on
the
dienes
employed.
The
performed
with
4‐substituted
produced
benzothiazolopyrimidines
as
major
product
yields
ranging
from
42
to
67%,
single
diastereoisomer
enantioselectivity
93
99%.
same
3‐substituted
dienes,
however,
gave
highly
enantioenriched
1,2,3,4‐tetrahydroquinolines
products
albeit
moderate
diastereoselectivity.
magnified
image
