A short and convenient synthesis and evaluation of the antiinfective properties of indoloquinoline alkaloids: 10H-Indolo[3,2-b]quinoline and 7H-indolo[2,3-c]quinolines
✍ Scribed by Jagan R. Etukala; E. V. K. Suresh Kumar; Seth Y. Ablordeppey
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2008
- Tongue
- English
- Weight
- 258 KB
- Volume
- 45
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
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10__H__‐Indolo[3,2‐b]quinoline and 7H‐indolo[2,3‐c]quinoline have been synthesized in two steps using a modified approach to our previous reported method. Starting from commercially available 3‐aminoquinoline and phenylboronic acid, the first step involved a copper acetate‐catalyzed coupling reaction and the second utilized a palladium acetate‐catalyzed intramolecular arylation reaction in the presence of trifluoroacetic acid as solvent. The anti‐infective activity of a selected number of the compounds was also evaluated.
📜 SIMILAR VOLUMES
## Abstract Treatment of 2‐hydroxy‐, 2‐mercapto‐, and 2‐ethoxycarbonylamino‐benzonitriles **12** with 2‐fluoro‐ or 2‐nitrophenacylbromides **13** under alkaline conditions provided the corresponding benzofuran, benzothiophene, and indole intermediates **10**, respectivelly. Nucleophilic cyclization
A new and a more efficient synthesis of \(10 \mathrm{H}\)-Indolo[3,2-b]quinoline (quindoline) is reported. The synthesis involved \(N\)-arylation of 3 -aminoquinoline with triphenylbismuth diacetate followed by oxidative cyclization using palladium(II) acetate. A selective \(N\)-alkylation methodolo