Synthesis of Dialkyl 4-Ethoxy-2,5-dihydro-1-(9,10-dihydro-9,10-dioxoanthracen-1-yl)-5-oxo-1H-pyrrole2,3-dicarboxylates |
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| Authors: | Issa Yavari Ali R. Alborzi Shoaleh Dehghan Farahnaz Nourmohammadian |
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| Affiliation: | 1. Department of Chemistry Science and Research Campus , Islamic Azad University, Tarbiat Modarres University , Tehran, Iran;2. Department of Chemistry , Science and Research Campus,Islamic Azad University , Tehran, Iran;3. Department of Colorant Manufacture , Iran Color Research Center , Tehran, Iran |
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| Abstract: | Abstract The reaction of ethyl 9,10-dihydro-9,10-dioxoanthracen-1-yl-carbamoyl-formate with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine leads to dialkyl 4-ethoxy-2,5-dihydro-1-(9,10-dihydro-9,10-dioxoanthracen-1-yl)-5-oxo-1H-pyrrole-2,3-dicarboxylates in fairly good yields. A dynamic NMR effect is observed as a result of restricted rotation around the single bond linking the anthraquinone moiety and the heterocyclic ring system, which is attributed to the interaction between the pyrrole residue and the peri C═O group. |
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| Keywords: | Intramolecular Wittig reaction peri interaction restricted rotation triphenylphosphine |
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