4.7 Article

I2-Catalyzed oxidative dehydrogenative tandem cyclization of 2-methylquinolines, arylamines and 1,4-dioxane

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 21, Pages 6108-6113

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo01125a

Keywords

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Funding

  1. Hunan Provincial Natural Science Foundation [2019JJ40057]
  2. Scientific Research Fund of Hunan Provincial Education Department [19A113]
  3. Opened-end Fund of Hunan Provincial Key Laboratory of Environmental Catalysis & Waste Recycling [2018KF05]

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In this novel I-2-catalyst oxidative dehydrogenative tandem cyclization reaction, 2-methylquinolines, arylamines, and 1,4-dioxane were used as substrates to construct 2-([2,2'-biquinolin]-3-yloxy)ethan-1-ol derivatives under metal-free conditions. This transformation involved the cleavage of 7 C-H bonds, 2 N-H bonds, and 1 C-O bond, leading to the formation of 2 C-C bonds, 1 C-N bond, and 1 O-H bond, with the opening of the 1,4-dioxane ring and the formation of a 2-(vinyloxy)ethan-1-ol group in the process.
A novel I-2-catalyst oxidative dehydrogenative tandem cyclization of three components, 2-methylquinolines, arylamines and 1,4-dioxane, for the construction of 2-([2,2 '-biquinolin]-3-yloxy)ethan-1-ol derivatives has been developed under metal-free conditions. This transformation with the cleavage of 7 C-H bonds, 2 N-H bonds and 1 C-O bond leads to the construction of 2 C-C bonds, 1 C-N bond and 1 O-H bond. The 1,4-dioxane ring was opened and a 2-(vinyloxy)ethan-1-ol group was obtained in the whole process.

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