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Iron/Zinc-Catalyzed Benzannulation Reactions of 2-(2-Oxo-alkyl)benzketones Leading to Naphthalene and Isoquinoline Derivatives

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) are 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.

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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, Accepted Manuscript
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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, Accepted Manuscript , DOI: 10.1039/C7QO01152K

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