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Facile synthesis of spiro thiazolidinone via cyclic ketones, amines and thioglycolic acid by MCM-41-Schiff base-CuSO4·5H2O

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Abstract

Mesoporous MCM-41-supported Schiff base and CuSO4·5H2O (MCM-41@Schiff base-CuSO4·5H2O) catalyzed one-pot three-component condensation of cyclic ketones, amines and thioglycolic acid in toluene. And a series of corresponding spiro thiazolidinone derivatives were obtained in high yields (up to 97%). The synthesized catalyst was characterized via FT-IR, XRD, SEM, TEM and EDS and can be easily recovered by centrifugation and reused at 10 times without any change in catalytic activity. Moreover, the scale-up experiment also demonstrated the practicability of the catalytic system on the condensation. The possible mechanisms pave the way to investigation on the reactions of other cyclic ketones with thioglycolic acid.

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Acknowledgements

The authors are grateful to the Special Fund for Outstanding Talented Young and Middle-aged Persons of Lingnan Normal University (No. ZL1908), Guangdong Natural Science Foundation (Grant Nos. 2018A030307022 and 2020A1515010252) and Adamas-beta Chemical Co. for all chemical reagents.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Key Laboratory of Clean Energy Materials Chemistry of Guangdong Higher Education Institute, Lingnan Normal University, Zhanjiang, 524048, China

    Yonghai Hui, Yongfei Zhang, Jianpeng Li, Yun Wang, Tianming Gao, Jialiang Xia, Sheng Wang & Shiqi Zhang

  2. Agriculture Products Processing Research Institute, Chinese Academy of Tropical Agriculture Science, Zhanjiang, 524001, China

    Yongyue Luo

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  1. Yonghai Hui
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Hui, Y., Zhang, Y., Luo, Y. et al. Facile synthesis of spiro thiazolidinone via cyclic ketones, amines and thioglycolic acid by MCM-41-Schiff base-CuSO4·5H2O. Res Chem Intermed 47, 521–532 (2021). https://doi.org/10.1007/s11164-020-04283-9

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