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Issue 23, 2009
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Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation

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Abstract

A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP.

Graphical abstract: Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation

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Publication details

The article was received on 06 Jul 2009, accepted on 09 Sep 2009 and first published on 06 Oct 2009


Article type: Paper
DOI: 10.1039/B913336D
Citation: Org. Biomol. Chem., 2009,7, 4960-4964
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    Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation

    K. M. Allan, B. D. Hong and B. M. Stoltz, Org. Biomol. Chem., 2009, 7, 4960
    DOI: 10.1039/B913336D

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