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One-pot Multicomponent Synthesis of Hydrazinyl Thiazoles Bearing an Isatin Moiety in Aqueous Medium
Journal
Letters in Organic Chemistry
ISSN
1570-1786
Date Issued
2024-02
Author(s)
Li-Ping Chung
Kit-Lin Tan
Yee-Ting Tan
Xin-Lee Kee
DOI
http://dx.doi.org/10.2174/1570178620666230914162955
Abstract
<jats:sec>
<jats:title>Abstract:</jats:title>
<jats:p>Isatin-derivatives are an important class of nitrogen-containing heterocyclic compounds in
organic synthesis. On the other hand, 1,3-thiazoles are 5-membered heterocyclic compounds containing
nitrogen and sulphur atoms. Hydrazinyl thiazoles are often prepared through the classical condensation
of aldehydes or ketones with thiosemicarbazide to yield thiosemicarbazones, which will then
undergo heterocyclization with phenylacyl bromides to give the corresponding hydrazinyl thiazoles.
Nowadays, multi-component reactions (MCRs) are considered the most powerful tool in organic synthesis.
The use of water as a green solvent in organic synthesis is one of the goals of green chemistry.
In this study, a series of new hydrazinyl thiazoles 3a-3u bearing an isatin moiety were synthesized in
good yield via a one-pot three-component condensation reaction of isatins with thiosemicarbazide and
phenyl acyl bromides in water under reflux condition. All the synthesized compounds were characterized
by IR, 1D-NMR, 2D-NMR and LC/MS spectral data.</jats:p>
</jats:sec>
<jats:title>Abstract:</jats:title>
<jats:p>Isatin-derivatives are an important class of nitrogen-containing heterocyclic compounds in
organic synthesis. On the other hand, 1,3-thiazoles are 5-membered heterocyclic compounds containing
nitrogen and sulphur atoms. Hydrazinyl thiazoles are often prepared through the classical condensation
of aldehydes or ketones with thiosemicarbazide to yield thiosemicarbazones, which will then
undergo heterocyclization with phenylacyl bromides to give the corresponding hydrazinyl thiazoles.
Nowadays, multi-component reactions (MCRs) are considered the most powerful tool in organic synthesis.
The use of water as a green solvent in organic synthesis is one of the goals of green chemistry.
In this study, a series of new hydrazinyl thiazoles 3a-3u bearing an isatin moiety were synthesized in
good yield via a one-pot three-component condensation reaction of isatins with thiosemicarbazide and
phenyl acyl bromides in water under reflux condition. All the synthesized compounds were characterized
by IR, 1D-NMR, 2D-NMR and LC/MS spectral data.</jats:p>
</jats:sec>
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