Issue 6, 2018

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) 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

Supplementary files

Article information

Article type
Research Article
Submitted
24 dec 2017
Accepted
09 jan 2018
First published
09 jan 2018

Org. Chem. Front., 2018,5, 1028-1033

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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