An alternative synthesis of 10H-indolo[3,2-b]quinoline and its selective N-alkylation

✍ Scribed by Pingchen Fan; Seth Y. Ablordeppey

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1997
• Tongue: English
• Weight: 470 KB
• Volume: 34
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570340624

✦ Synopsis

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 methodology for quindoline was also developed. Alkylation on (\mathrm{N}-5) was obtained in sulpholane, while alkylation on (\mathrm{N}-10) was achieved in acetone in the presence of potassium hydroxide. A sequential (\mathrm{N}-5) - and (\mathrm{N}-10) double alkylation procedure was also formulated.