Synthesis of Thieno[2,3‐b]quinolinone Derivatives |
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Authors: | Guang‐Fan Han Ming Wang Li‐Zhuang Chen Xiao‐Lei Hu |
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Affiliation: | Applied Chemistry, School of Biological and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212003, China |
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Abstract: | The Knoevenagel reactions of malononitrile with acetophenone or 4‐substituted acetophenons were carried to give the corresponding 2‐(1‐aryle thylidene)malononitriles, which was further cyclized with sulfur using NaHCO3 as catalysts to generate 2‐amino‐5‐arylthiophene‐3‐carbonitrile 2 . The intermediate enamines 3 were prepared by refluxing of 2 with 5‐substituted‐1,3‐cyclohexanedione using p‐toluenesulfonic acid as catalyst. The title compounds 4‐amino‐3‐aryl ‐7‐substituted‐7,8‐dihydrothieno[2,3‐b]quinolin‐5(6H)‐one were synthesized by cyclization of 3 in the presence of K2CO3 and Cu2Cl2. The structures of all compounds were characterized by elemental analysis, IR, MS, and 1H‐NMR spectra. |
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