Please use this identifier to cite or link to this item: http://nopr.niscair.res.in/handle/123456789/7536
Title: Synthesis and antimicrobial evaluation of ethoxyphthalimide derivatized spiro [indole-3,5′-(1,3)thiazolo(4,5-<i style="">c</i>)isoxazol]-2(1<i style="">H</i>)-ones <i style="">via</i> ring closure metathesis
Authors: Thadhaney, Bhawana
Sain, Devendra
Pemawat, Gangotri
Talesara, G L
Keywords: Isatin
2-aminopyridine
thiazolidinone
isoxazole
ω-bromoethoxyphthalimide
Issue Date: Mar-2010
Publisher: CSIR
Abstract: The synthesis of 3′-{(4-substituted phenyl-1-<i>N</i>-ethoxy­phthali­mido-6′-pyridin-2-yl}-3,3a′-dihydro-6′<i>H-</i>spiro[indole-3,5′-[1,3]­thi­a­zolo­[4,5-<i>c</i>]­isoxazol]-2(1<i>H</i>)-ones <b>6a-d </b>is carried out<b> </b>&nbsp;through a five step pathway starting from acid catalyzed condensation of 2-aminopyridine with isatin yielding 3-(pyridin-2-ylimino)-1,3-dihydro-2<i>H</i>-indol-2-one <b>1</b> which on reaction with thioacetic acid in the presence of anhydrous ZnCl<sub>2 </sub>give 3′-pyridin-2-yl-4′<i>H</i>-spiro[indole-3,2′-[1,3]­thiazolidine]-2,4′(1<i>H</i>)-dione <b>2</b>.<b> </b>Reaction of <b style="">2</b> with various aralde­hydes <b style="">3a-d</b> affords the corresponding 5′-[(4-substituted phenyl)­methylidene]-3′-pyridin-2-yl-4′<i>H</i>-spiro­[indole-3,2′-[1,3]­thiazoli­dine]-2,4′(1<i>H</i>)-diones <b>4a-d</b>. These chal­cones are further cyclised with hydroxylamine hydrochloride to furnish 3′-(4-substituted phenyl)-6′-pyridin-2-yl-3,3a′-dihydro-6′<i>H-</i>spiro[indole-3,5′-[1,3]thia­zolo[4,5-<i>c</i>]isoxazol]-2(1<i>H</i>)-ones <b>5a-d</b> which are subsequently condensed with ω-bromo­ethoxy­phthalimide to yield the targeted compounds <b style="">6a-d</b>. Structural confirmation of the synthesized compounds has been accomplished by IR, <sup>1</sup>H NMR, and mass spectral data. Final compounds have been screened for their antimicrobial activity.<b></b>
Description: 368-373
URI: http://hdl.handle.net/123456789/7536
Appears in Collections:IJC-B Vol.49B(03) [March 2010]

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