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Issue 1, 2009
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A facile synthesis of pyrrolo-(di)-benzazocinones via an intramolecular N-acyliminium ion cyclisation

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Abstract

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.

Graphical abstract: A facile synthesis of pyrrolo-(di)-benzazocinones via an intramolecular N-acyliminium ion cyclisation

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Publication details

The article was received on 01 Sep 2008, accepted on 10 Oct 2008 and first published on 12 Nov 2008


Article type: Paper
DOI: 10.1039/B815195D
Citation: Org. Biomol. Chem., 2009,7, 167-177
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    A facile synthesis of pyrrolo-(di)-benzazocinones via an intramolecular N-acyliminium ion cyclisation

    F. D. King, A. E. Aliev, S. Caddick, D. A. Tocher and D. Courtier-Murias, Org. Biomol. Chem., 2009, 7, 167
    DOI: 10.1039/B815195D

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