Please use this identifier to cite or link to this item: http://nopr.niscair.res.in/handle/123456789/9168
Title: Some electrophilic substitution reactions on 1-substituted-3-acetyl/carbethoxy-5-hydroxy-2-methylindole and the antimicrobial activity of these new indole derivatives
Authors: Donawade, Dundappa S
Gadaginamath, Guru S
Keywords: Electrophilic substitution reaction
methylindole
antimicrobial activity
indole derivatives
4-isogramines
Issue Date: Aug-2005
Publisher: CSIR
Series/Report no.: <b>Int</b>.<b>Cl</b>.<b><sup>7</sup> C 07 D 209/04 // 31/04, 31/10</b>
Abstract: Aminomethylation under Mannich reaction conditions on 3-carbethoxy-1-furfuryl-5-hydroxy-2-methylindole <b style="">1</b> and the corresponding bromo derivative <b style="">3</b> occurs regioselectively at C<sub>4</sub> position to furnish the 4-isogramines <b style="">2a-d</b>/<b style="">4a-d</b>. Nitration of 3-carbethoxy/acetyl-1-furfuryl-5-hydroxy-2-methylindoles <b style="">1/8</b> with hydrated ferric nitrate produces 3-carbethoxy/acetyl- 4, 6-dinitro-1-furfuryl-5-hydroxy-2-methylindoles <b style="">6/9</b>. Nitration of 4-isograamine <b style="">2 </b>and bromoindole <b style="">3</b> involves ipso-substitution and furnish the 4, 6-dinitroindole derivative <b style="">6</b> and not the expected 6-nitro-4-isogramine <b style="">5</b>/<b>6</b>-bromo-4-nitroindole <b style="">7</b>. However, nitration of 3.6-diacetylindoles <b style="">18a-d</b> and triacetylindole <b style="">10</b> yields 4-nitroindole derivatives <b style="">19a-d/11</b> wherein the acetyl group remain intact without involving in any ipso-substitution. Acetylation under Friedel-Crafts reaction conditions on 3-acetyl-1-furfuryl-5-hydroxy -2-methylindole <b style="">8</b> occurs at both C<sub>6</sub>-position of indole and C<sub>5</sub>-position of furan to furnish the triacetylindole <b style="">10</b>. Bromination of <b style="">1</b> with bromine in acetic acid or bromine in dioxane produces only 6-bromoindole <b style="">3</b>. The structures of all these newly synthesised compounds are confirmed by their spectral and analytical data and all these compounds are screened for antimicrobial activity.
Description: 1679-1685
URI: http://hdl.handle.net/123456789/9168
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.44B(08) [August 2005]

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