1301751-03-0Relevant articles and documents
Synthesis of N-vinyl substituted indoles and their acid-catalyzed behavior
Li, Hao,Boonnak, Nawong,Padwa, Albert
, p. 2062 - 2064 (2011)
A mild cross-coupling reaction has been used to access several N-vinyl substituted indoles. When treated with acid, these unique enamines produce novel dimeric and trimeric products derived from a preferred protonation reaction at the enamine π-bond.
N-alkenyl indoles as useful intermediates for alkaloid synthesis
Li, Hao,Boonnak, Nawong,Padwa, Albert
experimental part, p. 9488 - 9496 (2011/12/22)
A mild cross-coupling reaction to access several N-alkenyl-substituted indoles has been developed. The coupling procedure involves treating a NH-indole with various alkenyl bromides using a combination of 10 mol % of copper(I) iodide and 20 mol % of ethylenediamine as the catalyst in dioxane at 110 °C in the presence of K3PO4 as the base. When treated with acid, these unique enamines produce a dimeric product derived from a preferred protonation reaction at the enamine π-bond. A cationic cyclization reaction of the readily available 2-(2-(1H-indol-1-yl)allyl)cyclopentanol was utilized to construct tetracyclic indole derivatives with a quaternary stereocenter attached to the C2-position of the indole ring. An alternative strategy for selective functionalization at the C2-position of a N-alkenyl-substituted indole derivative that was also studied involves a radical cyclization of a xanthate derivative. The work described provides an attractive route to the tetracyclic core of some vinca alkaloids, including the tetrahydroisoquinocarbazole RS-2135.
