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An improved method for the preparation of 2-hydrazinylbenzo[d]thiazoles from benzo[d]thiazol-2-amines

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Title An improved method for the preparation of 2-hydrazinylbenzo[d]thiazoles from benzo[d]thiazol-2-amines
 
Creator Begum, Shahnaz
Bhimapaka, China Raju
 
Subject 2-Hydrazinylbenzo[d]thiazoles
Benzo[d]thiazol-2-amines
Hydrazine hydrate
 
Description 635-634
Hydrazinylbenzo[d]thiazoles are promising bio-active
heterocycles known for their use in pharmaceutical
and agrochemical industries1-4. This class of
compounds namely hydrazinylbenzo[d]thiazoletriapine
was identified as anti-cancer agents5. Further,
2-(2-(4-aryloxybenzylidene) hydrazinyl)benzothiazole
derivatives were reported as anti-tubercular agents6-8.
Benzothiazole based pyrene receptors9-12 displayed
fluorescent properties for the recognition of Zn2+3.
Consequently, the synthesis of hydrazinylbenzo[d]
thiazoles and their derivatives have attracted
considerable attention.
The 2-hydrazinylbenzo[d]thiazole was prepared by
reacting benzo[d]thiazol-2-amines with hydrazine
hydrate in presence of ethylene glycol as the solvent at
140°C13. To the best of our knowledge, ethylene glycol
is the only solvent used for the preparation of
2-hydrazinylbenzo[d]thiazole14. Ethylene glycol is not
a good solvent when handling the large scale
preparation of pharmaceutically important compounds.
Exposure of ethylene glycol can be extremely dangerous,
with significant morbidity and mortality if left untreated.
Therefore, there is a need to develop the method by
replacing the ethylene glycol solvent with other enviro
friendly solvent like water. In the course of our research
on heterocyclic compounds, we have reported various
heterocycles15-17 includingbenzohydrazides18. As part of
our research work on development of benzothiazole
heterocycles; we have conducted the reactions between
benzo[d]thiazol-2-amines and hydrazine hydrate in water
provided hydrazinylbenzo[d]thiazoles and the results are
discussed below.
 
Date 2024-06-21T11:28:53Z
2024-06-21T11:28:53Z
2024-06
 
Type Article
 
Identifier 2583-1321 (Online); 0019-5103 (Print)
http://nopr.niscpr.res.in/handle/123456789/64069
https://doi.org/10.56042/ijc.v63i6.10614
 
Language en
 
Publisher NIScPR-CSIR, India
 
Source IJC Vol.63(06) [June 2024]