122145-38-4Relevant academic research and scientific papers
Palladium-Catalyzed Reactions in the Synthesis of 3- and 4-Substituted Indoles
Hegedus, Louis S.,Sestrick, Michael R.,Michaelson, Eric T.,Harrington, Peter J.
, p. 4141 - 4146 (2007/10/02)
4-Bromo-1-tosylindole (1) was converted to tricyclic indole enone 11, a potential intermediate in the synthesis of tetracyclic ergot alkaloids, by a series of palladium-catalyzed processes.Attempts to construct the ergot D ring by the hetero-Diels-Alder reaction of enone 11 and 1-azabutadiene 12 produced not the expected adduct 13 but the benzindoline derivative 14 resulting from attack of the aza diene at the indole 2-position.The thermodynamic stability of the naphthol nucleus makes enone 11 generally susceptible to attack at the indole 2-position,as evidenced by the attack of hydride and methyl cuprate nucleophiles at this position forming indolines 16 and 17, respectively.
