Solvent-Free Synthesis of Novel Highly Functionalized Dihydroanthra[1,2-b]furan-6,11-dione Derivatives |
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Authors: | Farahnaz Nourmohammadian Mahnaz Davoodzadeh Gholami |
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Affiliation: | 1. Department of Organic Colorants , Institute for Colorants, Paint, and Coatings , Tehran, Iran nour@icrc.ac.ir;3. Department of Organic Colorants , Institute for Colorants, Paint, and Coatings , Tehran, Iran |
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Abstract: | A convenient and environmentally friendly solvent-free procedure has been developed to react 1,5-dihydroxyanthraquinone with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine in one pot to afford novel dialkyl (E)-2-{1,5-dihydroxy-6-[3-methoxy-1-(methoxycarbonyl)-3-oxo-2-(triphenyl-λ 5-phosphanylidene)propyl]-9,10-dioxo-9,10-dihydro-2-anthracenyl}-2-butanedioate 3a–c. As a result of intramolecular nucleophilic attack at 90 °C, novel dialkyl (E)-2–{2,7-dihydroxy-3-[2-methoxy-2-oxo-1-(triphenyl-λ 5 phosphanylidene)ethyl]-6,11-dioxo-6,11-dihydroanthra[1,2-b]furan-8-yl}-2-butanedioates 4a–c were produced in good yield. |
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Keywords: | Acetylenic ester C-vinylation 1 5-dihydroxyanthraquinone hydroxyfuran solvent free triphenylphosphine |
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