Construction of tetracyclic indole bases via Aza Diels-Alder reaction of indolylethylimines with Brassard's diene

✍ Scribed by Lock, Ralf ;Waldmann, Herbert

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 688 KB
• Volume: 1994
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.15619940511

✦ Synopsis

Abstract

Schiff's bases 3 derived from tryptamine react with Brassard's diene 4 in the presence of EtAlCl~2~ to give functionalized 1,2,5,6‐tetrahydropyridines which are subsequently transformed to indolo[2,3‐a]quinolizines 8–10 by the Bischler‐Napieralski reaction and reduction of the intermediate iminium salts with NaBH~4~. magnified image