Rhodium(II)-Catalyzed Intramolecular Annulation of 1-Sulfonyl-1,2,3-Triazoles with Pyrrole and Indole Rings: Facile Synthesis of N-Bridgehead Azepine Skeletons

Authors

  • Jin-Ming Yang,

    1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237 (China)
    Search for more papers by this author
  • Cheng-Zhi Zhu,

    1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237 (China)
    Search for more papers by this author
  • Dr. Xiang-Ying Tang,

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China)
    • Xiang-Ying Tang, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China)===

      Min Shi, Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237 (China)===

    Search for more papers by this author
  • Prof. Dr. Min Shi

    Corresponding author
    1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237 (China)
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China)
    • Xiang-Ying Tang, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China)===

      Min Shi, Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237 (China)===

    Search for more papers by this author

  • We are grateful for the financial support from the Shanghai Municipal Committee of Science and Technology (11JC1402600), the National Natural Science Foundation of China (20472096, 20872162, 20672127, 21372241, 21302203, 21361140350, 21121062, 20732008, and 20902019), the National Basic Research Program of China (973)-2010CB833302, and the Fundamental Research Funds for the Central Universities.

Abstract

A convenient and efficient synthetic method has been developed to construct highly functionalized N-bridgehead azepine skeletons, which are of great importance in biological and pharmaceutical industry. The reaction proceeds through a rhodium(II) azavinyl carbene intermediate, which initiated the intramolecular C[BOND]H functionalization with pyrrolyl and indolyl rings. A variety of azepine derivatives were obtained in moderate to good yields under mild reaction conditions with high chemoselectivity. Several interesting derivatizations of the resulting products demonstrate that this method is synthetically valuable and useful.

Ancillary