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Issue 6, 2018
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Iron/zinc-catalyzed benzannulation reactions of 2-(2-oxo-alkyl)benzketones leading to naphthalene and isoquinoline derivatives

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Abstract

An efficient method for the synthesis of poly-substituted naphthalene derivatives via Fe(III)-catalyzed [4 + 2] cycloaddition of 2-(2-oxo-alkyl)benzketones with alkynes or enols (generated in situ from alkyl aldehydes or alkyl ketones) is described. A variety of poly-substituted naphthalene derivatives could be synthesized in up to 90% yield under mild reaction conditions. Poly-substituted 1,2-dihydronaphthalene derivatives could be obtained instead through Zn(II)-catalyzed cyclization of 2-(2-oxo-alkyl)benzketones with alkenes. Furthermore, the Fe(III)-catalyzed intramolecular version could lead to isoquinoline derivatives in high yields.

Graphical abstract: Iron/zinc-catalyzed benzannulation reactions of 2-(2-oxo-alkyl)benzketones leading to naphthalene and isoquinoline derivatives

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Publication details

The article was received on 24 Dec 2017, accepted on 09 Jan 2018 and first published on 09 Jan 2018


Article type: Research Article
DOI: 10.1039/C7QO01152K
Citation: Org. Chem. Front., 2018,5, 1028-1033
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    Iron/zinc-catalyzed benzannulation reactions of 2-(2-oxo-alkyl)benzketones leading to naphthalene and isoquinoline derivatives

    C. Zhang, L. Chen, K. Chen, H. Jiang and S. Zhu, Org. Chem. Front., 2018, 5, 1028
    DOI: 10.1039/C7QO01152K

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