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Synthesis 2017; 49(07): 1547-1554
DOI: 10.1055/s-0036-1588668
DOI: 10.1055/s-0036-1588668
paper
Synthesis of Helical Quinone Derivatives by Oxidative Coupling of Substituted 2-Hydroxybenzo[c]phenanthrenes
Further Information
Publication History
Received: 16 October 2016
Accepted after revision: 11 November 2016
Publication Date:
11 January 2017 (online)
Abstract
A concise synthesis of novel substituted quinone derivatives from commercially available starting materials was developed. For this synthesis, classical photo-induced 6π-electrocyclization was utilized, followed by oxidative aromatization reaction, and subsequent oxidative coupling reactions in the presence of CuCl(OH)-TMEDA. The unique quinone derivatives were characterized by IR, 1H, and 13C NMR spectroscopies, and mass spectroscopic data analysis. In some cases, the keto dimers were obtained as significant intermediates for the quinone synthesis.
Key words
stilbenes - Siegrist reaction - Mallory reaction - oxidative coupling - quinones - helicenesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588668.
- Supporting Information
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