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Synthesis 2013; 45(3): 355-364
DOI: 10.1055/s-0032-1316829
DOI: 10.1055/s-0032-1316829
paper
Synthesis of Tricyclic Lactams from Heterocyclic Imines
Further Information
Publication History
Received: 13 October 2012
Accepted after revision: 28 November 2012
Publication Date:
21 December 2012 (online)
Abstract
Starting from different heterocyclic imines, a large number of annulated tricyclic lactams were prepared in a two-step synthesis. First, methoxyamides with a phenyl ring in α- or β-position were generated. Finally, these substrates were converted to valero- and caprolactams, respectively, via intramolecular Friedel–Crafts cyclization in the presence of a Lewis acid. Additionally, effects of substituent groups at the phenyl ring in the electrophilic aromatic substitution were investigated.
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For selected examples, see:
For excellent reviews dealing with reactive N-acyliminium ions, see: