Aza-Nazarov cyclization cascades

✍ Scribed by Kiran Kumar Solingapuram Sai; Matthew J. O’Connor; Douglas A. Klumpp

• Book ID: 104098707
• Publisher: Elsevier Science
• Year: 2011
• Tongue: French
• Weight: 954 KB
• Volume: 52
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.11.164

✦ Synopsis

Benzamides with tethered acetal groups undergo reactions in CF(3)SO(3)H to give ring-fused isoindolinones by a cyclization cascade. The reaction initially forms an N-acyliminium ion which then gives the isoindolinone by the aza-Nazarov reaction. An unusual variant also cyclizes at the allylic position.