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Chemoselective synthesis of β-enaminones from ynones and aminoalkyl-, phenol- and thioanilines under metal-free conditions

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Abstract

An effective strategy for the chemoselective synthesis of β-enaminones is described by aza-Michael addition of aminoalkyl-, phenol- and thio-anilines to ynones under metal-free conditions. Diverse structural β-enaminones were obtained in up to 99% yield for 31 examples. The novel dual-1,5-disubstituted triazole scaffold was synthesized subsequently from β-enaminone. This strategy is highly efficient, highly chemoselective and metal-free.

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Acknowledgements

Project supported by Hainan Provincial Nature Science Foundation of China (Nos. 2019RC214 & 820QN264), Fundamental Research Funds of Hainan Medical University (No. XRC180009) and the Program of Hainan Provincial Key Laboratory for Research and Development of Tropical Herbs (No. KF201804).

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Correspondence to Xuesong Wang.

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Cui, X., Chen, Y., Wang, W. et al. Chemoselective synthesis of β-enaminones from ynones and aminoalkyl-, phenol- and thioanilines under metal-free conditions. Chem. Pap. 75, 3625–3634 (2021). https://doi.org/10.1007/s11696-021-01599-7

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  • DOI: https://doi.org/10.1007/s11696-021-01599-7

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