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Selective Iodine-Catalyzed Intermolecular Oxidative Amination of C(sp3)[BOND]H Bonds with ortho-Carbonyl-Substituted Anilines to Give Quinazolines

Authors

  • Dr. Yizhe Yan,

    1. Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China)
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  • Yonghui Zhang,

    1. Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China)
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  • Dr. Chengtao Feng,

    1. Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China)
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  • Prof. Zhenggen Zha,

    1. Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China)
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  • Prof. Dr. Zhiyong Wang

    Corresponding author
    1. Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China)
    • Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China)
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  • We are grateful to the Natural Science Foundation of China (20932002, 207721118, and 20972144) and the Ministry of Science & Technology of China (2010CB912103), and the support from the Chinese Academy of Sciences.

Abstract

original image

Access to quinazolines: The selective amination of C(sp3)[BOND]H bonds adjacent to nitrogen or oxygen atoms of N-alkylamides, ethers, or alcohols with ortho-carbonyl-substituted anilines constitutes the first step in a tandem annulation that leads to quinazolines in good to excellent yields (see scheme; NIS=N-Iodosuccinimide, TBHP=tert-butyl hydroperoxide). The selectivity of the amination of primary and secondary C[BOND]H bonds is also noteworthy (left: >3:1, right: >99:1).

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