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IJC-B Vol.44B(08) [August 2005] >


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
IPC CodeInt.Cl.7 C 07 D 209/04 // 31/04, 31/10
Abstract: Aminomethylation under Mannich reaction conditions on 3-carbethoxy-1-furfuryl-5-hydroxy-2-methylindole 1 and the corresponding bromo derivative 3 occurs regioselectively at C4 position to furnish the 4-isogramines 2a-d/4a-d. Nitration of 3-carbethoxy/acetyl-1-furfuryl-5-hydroxy-2-methylindoles 1/8 with hydrated ferric nitrate produces 3-carbethoxy/acetyl- 4, 6-dinitro-1-furfuryl-5-hydroxy-2-methylindoles 6/9. Nitration of 4-isograamine 2 and bromoindole 3 involves ipso-substitution and furnish the 4, 6-dinitroindole derivative 6 and not the expected 6-nitro-4-isogramine 5/6-bromo-4-nitroindole 7. However, nitration of 3.6-diacetylindoles 18a-d and triacetylindole 10 yields 4-nitroindole derivatives 19a-d/11 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 8 occurs at both C6-position of indole and C5-position of furan to furnish the triacetylindole 10. Bromination of 1 with bromine in acetic acid or bromine in dioxane produces only 6-bromoindole 3. 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.
Page(s): 1679-1685
ISSN: 0975-0983(Online); 0376-4699(Print)
Source:IJC-B Vol.44B(08) [August 2005]

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