Synlett 2017; 28(14): 1821-1827
DOI: 10.1055/s-0036-1589009
letter
© Georg Thieme Verlag Stuttgart · New York

Poly(phosphoric acid) (PPA)-Promoted 5-exo-Cyclization of Iminium Ions Generated In Situ: A Facile Access to Functionalized Indene Derivatives

Authors

  • Yi-Fan Zhu

    a   School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, P. R. of China   Email: fanxh@mail.lzjtu.cn
  • Xin-Le Geng

    a   School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, P. R. of China   Email: fanxh@mail.lzjtu.cn
  • Yong-Hong Guan

    a   School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, P. R. of China   Email: fanxh@mail.lzjtu.cn
  • Wei Teng

    a   School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, P. R. of China   Email: fanxh@mail.lzjtu.cn
  • Xiaohui Fan*

    a   School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, P. R. of China   Email: fanxh@mail.lzjtu.cn
    b   Beijing National Laboratory for Molecular Sciences (BNLMS), College of Chemistry, Peking University, Beijing 100871, P. R. of China
    c   YMU-HKBU Joint Laboratory of Traditional Natural Medicine, Yunnan Minzu University, Kunming 650500, P. R. of China

Supported by: National Natural Science Foundation of China (21162013), (21562030) Supported by: Beijing National Laboratory for Molecular Sciences (20140133)
Further Information

Publication History

Received: 21 January 2017

Accepted after revision: 26 March 2017

Publication Date:
04 May 2017 (online)


Graphical Abstract

Abstract

A metal-free Brønsted acid promoted two-component reaction between cinnamaldehydes and sulfonamides is described. This cascade process provides a simple and atom-economical alternative synthesis of a range of functionalized indenes from easily available starting materials. The resulting N-indenylsulfonamides were readily converted into the corresponding indenylenamines or indanones.

Supporting Information