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Issue 17, 2009
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An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: a facile synthesis of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones

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Abstract

The triflic acid-mediated cyclisation of N-arylmethyl- and N-arylethyl-acylpyrrolidinium ions gave moderate to good yields of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones respectively. Electron-donating R substituents enhanced the rate of reaction and gave higher yields than electron-withdrawing substituents. Substituents on the methyl or ethyl chain in general enhanced the reaction, unless sterically encumbered. The equivalent acylpiperidinium ions cyclised much slower and in lower yield.

Graphical abstract: An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: a facile synthesis of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones

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Publication details

The article was received on 14 Apr 2009, accepted on 10 Jun 2009 and first published on 09 Jul 2009


Article type: Paper
DOI: 10.1039/B907400G
Citation: Org. Biomol. Chem., 2009,7, 3561-3571
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    An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: a facile synthesis of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones

    F. D. King, A. E. Aliev, S. Caddick and R. C. B. Copley, Org. Biomol. Chem., 2009, 7, 3561
    DOI: 10.1039/B907400G

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