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Issue 20, 2011
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Practical three-component synthesis of crowded arenes with donor–acceptor substitution

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Abstract

An operationally simple two-step synthesis of substituted anilides has been developed. The methodology utilizes carboxamides, aldehydes, and olefins (or alkynes) as cheap starting materials and relies upon the sequential combination of condensation, cycloaddition, and oxidation reactions. The intermediate cycloadducts display various functional groups (e.g. Br, OAc, NR2, COR, Cbz) for further chemical manipulation at the ring periphery or core. Upon oxidation with MnO2, highly crowded anilides with up to four further substituents (alkyl, aryl, carboxylate, cyano, nitro, bromo) can be prepared in good overall yields.

Graphical abstract: Practical three-component synthesis of crowded arenes with donor–acceptor substitution

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Publication details

The article was received on 17 Jun 2011, accepted on 19 Jul 2011 and first published on 30 Aug 2011


Article type: Paper
DOI: 10.1039/C1OB05984J
Citation: Org. Biomol. Chem., 2011,9, 7224-7236
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    Practical three-component synthesis of crowded arenes with donor–acceptor substitution

    R. Fichtler, Jörg-M. Neudörfl and A. Jacobi von Wangelin, Org. Biomol. Chem., 2011, 9, 7224
    DOI: 10.1039/C1OB05984J

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