Amidoalkylation reactions of anilines. A direct synthesis of benzodiazepinesThe Journal of Organic Chemistry
Publication VersionPublished Version
AbstractIntermolecular amidoalkylation reactions on aromatic rings constitute an effective strategy for the construction of heterocyclic c0mpounds.l A variety of substituents, including nitro groups, can be accommodated on the aromatic ring. However, anilines or acetanilides react with acyl iminium ions to afford mixtures of products in only modest yields.2 Moreover, the reactions with both o- and p-toluidine yield products wherein the position of substitution of the electrophile is directed by the methyl groupq3 This reactivity profile is due to deactivation by the iminium salt that is produced either by protonation in an acid-catalyzed reaction or by complexation with the Lewis acid catalyst.
Copyright OwnerAmerican Chemical Society
Citation InformationGeorge A. Kraus and Stephen Yue. "Amidoalkylation reactions of anilines. A direct synthesis of benzodiazepines" The Journal of Organic Chemistry Vol. 48 Iss. 17 (1983) p. 2936 - 2937
Available at: http://works.bepress.com/george_kraus/32/