Synthesis of fused bicyclic glutarimides |
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Authors: | Meng-Yang Chang Chung-Yi ChenShui-Tein Chen Nein-Chen Chang |
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Affiliation: | a Department of Applied Chemistry, National University of Kaohsiung, Kaohsiung 811, Taiwan, ROC b Department of Chemistry, National Sun Yat-Sen University, Kaohsiung 804, Taiwan, ROC c Institute of Biological Chemistry, Academia Sinica, Nankang, Taipei 115, Taiwan, ROC |
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Abstract: | We describe an efficient route towards the synthesis of fused bicyclic glutarimides using facile [3+3] reaction of α-sulfonylacetamides with different α,β-unsaturated esters as the key step. Intramolecular cyclization of 4-substituted 3-sulfonylglutarimide to form 5,6-, 6,6- or 6,7-fused bicyclic glutarimides was accomplished via alkylation, oxidative cyclization or ring-closing metathesis in modest yield. |
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Keywords: | bicyclic glutarimides stepwise [3+3] annulation intramolecular alkylation oxidative cyclization or ring-closing metathesis |
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