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Issue 39, 2018
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FeCl3-promoted tandem 1,4-conjugate addition/6-endo-dig cyclization/oxidation of propargylamines and benzoylacetonitriles/malononitriles: direct access to functionalized 2-aryl-4H-chromenes

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Abstract

An efficient and concise procedure has been developed for the synthesis of functionalized 2-aryl-4H-chromenes based on a tandem reaction of propargylamines and benzoylacetonitriles/malononitriles in the presence of FeCl3 as an environmentally friendly promoter. This reaction involves a highly efficient tandem sequence consisting of 1,4-conjugate addition, 6-endo-dig cyclization, and oxidation. This protocol tolerates a variety of functional groups, thereby providing a practical and efficient method for the fabrication of 2-aryl-4H-chromene skeletons.

Graphical abstract: FeCl3-promoted tandem 1,4-conjugate addition/6-endo-dig cyclization/oxidation of propargylamines and benzoylacetonitriles/malononitriles: direct access to functionalized 2-aryl-4H-chromenes

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Publication details

The article was received on 07 Aug 2018, accepted on 07 Sep 2018 and first published on 08 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB01927D
Citation: Org. Biomol. Chem., 2018,16, 7191-7202
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    FeCl3-promoted tandem 1,4-conjugate addition/6-endo-dig cyclization/oxidation of propargylamines and benzoylacetonitriles/malononitriles: direct access to functionalized 2-aryl-4H-chromenes

    X. He, H. Wang, X. Cai, Q. Li, J. Tao and Y. Shang, Org. Biomol. Chem., 2018, 16, 7191
    DOI: 10.1039/C8OB01927D

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