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Issue 41, 2015
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Organocatalyzed benzannulation for the construction of diverse anthraquinones and tetracenediones

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Abstract

An efficient one-pot synthesis of anthraquinones and tetracenediones was achieved viaL-proline catalyzed [4+2] cycloaddition of in situ generated azadiene from α,β-unsaturated aldehydes and 1,4-naphthoquinones or 1,4-anthracenedione in good to excellent yield. This protocol constitutes an unprecedented tandem benzannulation that allows one-pot construction of diverse anthraquinones and tetracenediones in the presence of organocatalysts. This methodology was applied successfully to the synthesis of naturally occurring molecules and photochemically interesting phenanthrenequinone derivatives.

Graphical abstract: Organocatalyzed benzannulation for the construction of diverse anthraquinones and tetracenediones

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Publication details

The article was received on 24 Jan 2015, accepted on 01 Apr 2015 and first published on 10 Apr 2015


Article type: Communication
DOI: 10.1039/C5CC00623F
Chem. Commun., 2015,51, 8592-8595

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    Organocatalyzed benzannulation for the construction of diverse anthraquinones and tetracenediones

    K. B. Somai Magar, L. Xia and Y. R. Lee, Chem. Commun., 2015, 51, 8592
    DOI: 10.1039/C5CC00623F

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