29-Jul-2010
16:05:57 IST
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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.49B [2010] >
IJC-B Vol.49B(03) [March 2010] >
| Title: | Synthesis and antimicrobial evaluation of ethoxyphthalimide derivatized spiro [indole-3,5′-(1,3)thiazolo(4,5-c)isoxazol]-2(1H)-ones via 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-N-ethoxyphthalimido-6′-pyridin-2-yl}-3,3a′-dihydro-6′H-spiro[indole-3,5′-[1,3]thiazolo[4,5-c]isoxazol]-2(1H)-ones
6a-d is carried out through a five step pathway starting from acid
catalyzed condensation of 2-aminopyridine with isatin yielding
3-(pyridin-2-ylimino)-1,3-dihydro-2H-indol-2-one 1 which on
reaction with thioacetic acid in the presence of anhydrous ZnCl2 give
3′-pyridin-2-yl-4′H-spiro[indole-3,2′-[1,3]thiazolidine]-2,4′(1H)-dione
2. Reaction of 2 with
various araldehydes 3a-d affords
the corresponding 5′-[(4-substituted phenyl)methylidene]-3′-pyridin-2-yl-4′H-spiro[indole-3,2′-[1,3]thiazolidine]-2,4′(1H)-diones
4a-d. These chalcones are further cyclised with hydroxylamine
hydrochloride to furnish 3′-(4-substituted phenyl)-6′-pyridin-2-yl-3,3a′-dihydro-6′H-spiro[indole-3,5′-[1,3]thiazolo[4,5-c]isoxazol]-2(1H)-ones
5a-d which are subsequently condensed with ω-bromoethoxyphthalimide to
yield the targeted compounds 6a-d.
Structural confirmation of the synthesized compounds has been accomplished by
IR, 1H NMR, and mass spectral data. Final compounds have been screened
for their antimicrobial activity. |
| Page(s): | 368-373 |
| Source: | IJC-B Vol.49B(03) [March 2010]
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