Under solvent-free conditions, syntheses of 2-aryl-4-(4-β-D-allopyranosyloxyphenyl)-4,6,7,8tetrahydroquinolin-5(1H)-one derivatives were carried out from chalcone (2a–2e), cyclohexane-1,3-dione (3), and NH4OAc in excellent yield without using any catalysts. The structure of the new compounds were characterized by 1H NMR, IR, and HR-MS spectroscopy. The preliminary bioassay tests of 4a–4j indicated that compounds 4b, 4e, and 4f exhibited potent sedative and hypnotic activity.
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Acknowledgment
The authors thank the Analytical & Testing Center, Sichuan University, P. R. China for assistance in obtaining analytical data, and Mr. Bao (Department of Pharmacy, Sichuan University) who performed the sedative-hypnotic tests.
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Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 775–778, November–December, 2010.
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Yang, C., Lv, S., Li, Y. et al. Synthesis of 2-aryl-4-(4-β-D-allopyranosyloxyphenyl)4,6,7,8-tetrahydroquinolin-5(1H)-one derivatives under solvent-free conditions and study of sedative activity. Chem Nat Compd 46, 910–914 (2011). https://doi.org/10.1007/s10600-011-9781-z
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DOI: https://doi.org/10.1007/s10600-011-9781-z