Selective synthesis of 2-(5-oxo-1-arylhex-1-yn-3-yl)phenyl benzoates via FeCl3-mediated cascade reactions of propargylamines with β-enamino ketones |
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| Authors: | Qiang Tang Xinwei He Jinxue Zhang Tongtong Zhou Mengqing Xie Ruxue Li Youpeng Zuo Yongjia Shang |
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| Institution: | Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu, 241002 People's Republic of China |
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| Abstract: | A mild and efficient FeCl3-mediated cascade reaction of ortho-hydroxyl propargylamines with β-enamino ketones has been developed. This protocol provided a practical and selective method to synthesize 2-(5-oxo-1-arylhex-1-yn-3-yl)phenyl benzoates via in situ generated alkynyl o-quinone methides following a cascade intermolecular 1,4-conjugate addition/intramolecular nucleophilic addition/reverse Claisen condensation/hydrolysis pathway. Furthermore, a series of 2-(3-oxo-1-arylbutyl)phenyl benzoates with good functional group tolerance were prepared in good to high yields under these reaction conditions. |
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| Keywords: | benzoates cascade reaction propargylamines quinone methides β-enamino ketones |
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