Skip to main content
Article
Amidoalkylation reactions of anilines. A direct synthesis of benzodiazepines
The Journal of Organic Chemistry
  • George A. Kraus, Iowa State University
  • Stephen Yue, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
8-1-1983
DOI
10.1021/jo00165a034
Abstract

Intermolecular 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.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 48(17); 2936-2937. Doi: 10.1021/jo00165a034. Copyright 1983 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
George 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/