Synthesis of 2-substituted 9,10-anthraquinones |
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Authors: | Meng-Yang Chang Hang-Yi Tai |
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Affiliation: | 1. Department of Medicinal and Applied Chemistry , Kaohsiung Medical University , Kaohsiung , Taiwan mychang@kmu.edu.tw;3. Department of Medicinal and Applied Chemistry , Kaohsiung Medical University , Kaohsiung , Taiwan |
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Abstract: | A convenient preparation of racemic 2-substituted 9,10-anthraquinones that included 2-triazoylethyl skeleton 1 and 2-alkylethyl skeleton 6 is reported. The products were obtained in good yields by a three- or four-step synthetic route based on a sequence of N-bromosuccinimide (NBS)–mediated bromination of 2-ethyl-9,10-anthraquinone 2, nucleophilic substitution, and CuI-catalyzed 1,3-dipolar cycloaddition or alkylation/reductive desulfonylation. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] |
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Keywords: | Alkynes azides dipolar cycloaddition heterocycles nucleophilic substitution |
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