|
NISCAIR ONLINE PERIODICALS REPOSITORY (NOPR) >
NISCAIR PUBLICATIONS >
Research Journals >
Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.44B [2005] >
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 Code: | Int.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]
|
|
