TiCl4/t-BuNH2-Promoted Hydroamination/Annulation of δ-Keto-acetylenes:  Synthesis of Novel Pyrrolo[1,2-a]indol-2-carbaldehydes

TiCl4/t-BuNH2-Promoted Hydroamination/Annulation of δ-Keto-acetylenes:  Synthesis of Novel Pyrrolo[1,2-a]indol-2-carbaldehydes

An original TiCl4/t-BuNH2-mediated hydroamination/annulation domino reaction of δ-keto-acetylenes is described. The synthesis of pyrrolo[1,2-a]indole-2-carbaldehydes, starting from 2-carbonyl-1-propargyl-1H-indoles runs under mild reaction conditions. A conceivable mechanism is also discussed. TiCl4...

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Veröffentlicht in:Organic letters 2006-10, Vol.8 (21), p.4839-4842
Hauptverfasser: Abbiati, Giorgio, Casoni, Alessandro, Canevari, Valentina, Nava, Donatella, Rossi, Elisabetta
Format: Artikel
Sprache:eng
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Zusammenfassung:An original TiCl4/t-BuNH2-mediated hydroamination/annulation domino reaction of δ-keto-acetylenes is described. The synthesis of pyrrolo[1,2-a]indole-2-carbaldehydes, starting from 2-carbonyl-1-propargyl-1H-indoles runs under mild reaction conditions. A conceivable mechanism is also discussed. TiCl4 has proved to be an effective multiactivity reagent:  catalyst/Lewis acid/water scavenger. Some unpublished 2-carbonyl-1-propargyl-1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol061872u