Article
Metal-Free Tandem Beckmann–Electrophilic Aromatic Substitution Cascade Affording Diaryl Imines, Ketones, Amines, and Quinazolines
Tetrahedron Letters
Document Type
Article
Publication Date
8-1-2015
Pages
5390-5392
Publisher Name
Elsevier
Disciplines
Abstract
A cascade reaction sequence involving a Beckmann rearrangement on benzophenone oxime followed by an electrophilic aromatic substitution (EAS) on the intermediate nitrilium ion affords N-phenyl diaryl imines that may then be hydrolyzed to ketones, or reduced to the corresponding amines. Reaction with benzonitrile afforded 2,4-diphenylquinazoline through a Beckmann–Ritter–EAS cascade.
Creative Commons License
Creative Commons Attribution-Noncommercial-No Derivative Works 3.0
Copyright Statement
© Elsevier Ltd. 2015
Citation Information
Samuel Sarsah, Marlon R. Lutz, Kailyn Chichi Bobb and Daniel Becker. "Metal-Free Tandem Beckmann–Electrophilic Aromatic Substitution Cascade Affording Diaryl Imines, Ketones, Amines, and Quinazolines" Tetrahedron Letters Vol. 56 Iss. 40 (2015) Available at: http://works.bepress.com/daniel_p_becker/41/
Author Posting. © Elsevier Ltd. 2015. This is the author's version of the work. This article is posted here by permission of Elsevier for personal use, not for redistribution. The article was published in Tetrahedron Letters, vol. 60, no. 40, 2015, https://doi.org/10.1016/j.tetlet.2015.07.095.