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A Novel Construction of 2‐Benzazepine Scaffold Based on TiCl 4 ‐Mediated Tandem Mannich Reaction–Aromatic Electrophilic Substitution
Author(s) -
Li Liangxi,
Li Zhiming,
Wang Quanrui
Publication year - 2009
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200900107
Subject(s) - benzazepine , chemistry , iminium , tandem , tricyclic , alkylation , medicinal chemistry , friedel–crafts reaction , benzazepines , electrophilic aromatic substitution , mannich reaction , combinatorial chemistry , organic chemistry , stereochemistry , ion , catalysis , materials science , composite material
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[3,2‐ d ][2]benzazepine derivatives, respectively, with 2,3‐dihydrofuran or 3,4‐dihydro‐2 H ‐pyran as the substrates.