Microwave-assisted traceless synthesis of hydantion-fused β-carboline scaffold |
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Authors: | Wen-Pin Yeh Mei-Lian Sun Chung-Ming Sun |
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Institution: | a Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300, Taiwan, ROC b Department of Kinesiology and Health Studies, National University of Kaohsiung, Kaohsiung 811, Taiwan, ROC |
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Abstract: | Multistep microwave-assisted reactions toward the synthesis of hydantoin-fused tricyclic tetrahydro-β-carbolines on the soluble polymer support have been developed. Polymer-bound tryptophan with various aldehydes has been subjected to Pictet-Spengler reaction to obtain tricyclic β-carboline conjugates. The terminal hydantoinyl moiety is constructed across polymer-bound β-carbolines by the reaction with various isocyanates under microwave irradiation to form urea intermediate. Simultaneous intramolecular cyclization of urea followed by cleavage of the polymer support leads to a traceless synthesis of tetracyclic scaffolds in high yield and high purity. |
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