A Novel Construction of 2-Benzazepine Scaffold Based on TiCl4-Mediated Tandem Mannich Reaction–Aromatic Electrophilic Substitution

✍ Scribed by Liangxi Li; Zhiming Li; Quanrui Wang

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: German
• Weight: 187 KB
• Volume: 92
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200900107

✦ Synopsis

A novel construction of 2-benzazepine derivatives based on TiCl 4 -mediated tandem Mannich reaction of electron-rich benzyl iminium ions with alkenyl ethers and Friedel -Crafts-type alkylation is described. The protocol is amenable to provide the tricyclic furo [3,2-d][2]benzazepine and pyrano [3,2d][2]benzazepine derivatives, respectively, with 2,3-dihydrofuran or 3,4-dihydro-2H-pyran as the substrates.

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