1111702-16-9Relevant academic research and scientific papers
A facile synthesis of pyrrolo-(di)-benzazocinones via an intramolecular N-acyliminium ion cyclisation
King, Frank D.,Aliev, Abil E.,Caddick, Stephen,Tocher, Derek A.,Courtier-Murias, Denis
experimental part, p. 167 - 177 (2009/04/07)
A facile, moderate to high yielding synthesis of hexahydro-(di)- benzazocinones is described via an intramolecular N-acyliminium ion cyclisation. The iminium ion intermediates are formed from the readily available 4,4-diethoxybutyl amides with an excess of triflic acid. For electron-withdrawing substituents, better yields were obtained from the pre-formed 2-hydroxypyrrolidine amides. From NMR studies, at ambient temperatures the pyrrolo-benzazocin-3-ones exist as a slowly equilibrating mixture of two conformations.
