Triethylamin-mediated addition of 2-aminoethanethiol hydrochloride to chalcones: Synthesis of 3-(2-aminoethylthio)-1-(aryl)-3-(thiophen-2-yl) propan-1-ones and 5,7-diaryl-2,3,6, 7-tetrahydro-1,4-thiazepines |
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Authors: | Meliha Burcu Gürdere Ali Cemal Emeç Osman Nuri Aslan Yakup Budak Mustafa Ceylan |
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Institution: | 1. Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat, Turkeyburcu.gurdere@gop.edu.tr;3. Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat, Turkey |
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Abstract: | The triethylamin-mediated addition of 2-aminoethanethiol hydrochloride to chalcone analogs was investigated. This addition, bearing a 2-thienyl group at the 3-position, gave the only addition adduct at room temperature in 3 h, whereas the chalcones bearing the 2-furyl group at the 1-position gave an addition-cyclization product (1, 4-thiazepine) in the same conditions. The effect of the groups to the reaction was investigated by changing the 1- and 3-position groups. The chalcones bearing the 2-thienyl group at the 1-position and the others afforded the mixture of products in different ratio at rt for 0.5–24 h. Moreover, the addition–cyclization products (1,4-thiazepine) were obtained under reflux conditions in 36 h. The structures of the synthesized compounds were elucidated by 1H NMR, 13C NMR, infrared, and elemental analysis. |
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Keywords: | 2-Aminoethanethiol hydrochloride chalcones 1 4-thiazephines triethylamin |
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