40900-03-6Relevant articles and documents
Synthesis of Prenylated Indoles
Wenkert, Ernest,Angell, E. Charles,Ferreira, Vitor F.,Michelotti, Enrique L.,Piettre, Serge R.,et al.
, p. 2343 - 2351 (2007/10/02)
Interaction of magnesium indolates and allyl oxides in the presence of bis(triphenylphosphine)nickel dichloride results in indole β-allylation, except in cases involving highly substituted indoles and allyl alcohols.This method permits the β-prenylation of indole and α-prenylation of ketones (by way of their magnesium enaminates).Base-induced interaction of ethynyldimethylcarbinyl chloride and indole under a variety of conditions yields β-(β,β-dimethylvinyl)quinoline as well as variously dehydroprenylated indoles. α-Lithiation of N-(benzenesulfonyl)indole followed by treatmentwith prenyl bromide or β,β-dimethylacrylyl chloride produces α-prenyl- or α-oxoprenylidole derivatives, the sodium amalgam reduction of the former of which yields α-prenylidole.Interaction of β-cuprated N-(benzenesulfonyl)indole with the same halides followed by reduction affords β-prenylindole and β-oxoprenylindole, the latter also being the product of the reaction of magnesium indolate and the acid chloride.Lithium aluminum hydride reduction of 1-(benzenesulfonyl)-3-oxoprenylindole affords an alcohol, whose base hydrolysis produces β-dehydroprenylindole, a compound whose dimerization has led previously to naturally occuring yuehchukene.
Generation and Reactions of 3-Lithio-1-(phenylsulfonyl)indole
Saulnier, Mark G.,Gribble, Gordon W.
, p. 757 - 761 (2007/10/02)
Treatment of 1-(phenylsulfonyl)-3-iodoindole (6) with 2 equiv of tert-butyllithium (-100 deg C THF) generates essentially quantitatively 3-lithio-1-(phenylsulfonyl)indole (1).Quenching 1 with various electrophiles gives 3-substituted indoles in good yield
