Diels-Alder Reactions of (1H-Indol-3-yl)-enacetamides and -endiacetamides: A Selective Access to Acetylamino-Functionalized [b]Annelated Indoles and Carbazoles

✍ Scribed by Ulf Pindur; Christian Otto; Michel Molinier; Werner Massa

• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: German
• Weight: 750 KB
• Volume: 74
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19910740406

✦ Synopsis

Diels-Alder reactions of the (lH-indol-3-yl)-enacetamides and -endiacetamides l a 4 with some carbodienophiles and 4-phenyl-3H-l,2,4-triazole-3,5(4H)-dione give rise to the novel amino-functionalized carbazoles 4 6 and 8 (Scheme 3). Ethenetetracarbonitrile reacts with l b to furnish the Michael-type adduct 7 (Scheme 3). Structural aspects of the starting materials 1, which exhibit above all 3-vinyl-1H-indole reactivity, are discussed with regard to the prediction of a Diels-Alder process.