Metal-free tandem Beckmann-electrophilic aromatic substitution cascade affording diaryl imines, ketones, amines, and quinazolines

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• 作者：Samuel R.S. Sarsah^&dagger ; ; ^{samuelsarsah@yahoo.com" class="auth_mail" title="E-mail the corresponding author} ; Marlon R. Lutz Jr.^&Dagger ; ; ^{mlutz@registech.com" class="auth_mail" title="E-mail the corresponding author} ; Kailyn Chichi Bobb ; Daniel P. Becker ; ^{dbecke3@luc.edu" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Cascade reaction ; Tandem sequence ; Beckmann rearrangement ; Electrophilic aromatic substitution ; Quinazoline
• 刊名：Tetrahedron Letters
• 出版年：2015
• 出版时间：30 September 2015
• 年：2015
• 卷：56
• 期：40
• 页码：5390-5392
• 全文大小：431 K

文摘

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.