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Aza-Nazarov cyclization cascades.

ABSTRACT: 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.

SUBMITTER: Sai KK

PROVIDER: S-EPMC3109674 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Aza-Nazarov cyclization cascades.

Sai Kiran Kumar Solingapuram KK O'Connor Matthew J MJ Klumpp Douglas A DA

Tetrahedron letters 20110401 17

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. ...[more]

PMID: 21660198

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