Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (3): 724-730.DOI: 10.6023/cjoc201409032 Previous Articles     Next Articles



吴玉芹a, 于凉云a, 张奇a, 李立冬a,b   

  1. a 盐城工学院化学与生物工程学院 盐城 224051;
    b 安徽师范大学化学与材料科学学院 芜湖 241000
  • 收稿日期:2014-09-20 修回日期:2014-10-15 发布日期:2014-11-07
  • 通讯作者: 李立冬
  • 基金资助:

    国家自然科学基金(No. 21272005)资助项目.

Simple Synthesis of Arylamines from Tetraynes via the Hexadehydro-Diels-Alder Reaction

Wu Yuqina, Yu Liangyuna, Zhang Qia, Li Lidonga,b   

  1. a School of Chemical and Biological Engineering, Yancheng Institute of Technology, Yancheng 224051;
    b College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000
  • Received:2014-09-20 Revised:2014-10-15 Published:2014-11-07
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272005).

Arylamines are widespread in natural products, pharmaceuticals and molecular materials, and are useful synthetic building blocks. From a synthetic standpoint, the formation of Caryl—N bonds has been achieved by classical methods such as nucleophilic aromatic substitution, electrophilic nitration/reduction, or the transition-metal-mediated arylation of amides. This paper describes an efficient method for the synthesis of arylamines by the hexadehydro-Diels-Alder (HDDA) reaction of tetraynes under catalyst-free condition. This process is achieved in the absence of metal catalyst, base or oxidant, and it does not require the pre-installation of directing groups. This reaction exhibited an excellent regioselectivity, producing highly substituted fused yne-functionalized bicyclic compounds under mild conditions with good to excellent yields. All new products were fully characterized by various spectroscopic techniques and high-resolution mass spectrometry. The molecular structure of 3h was confirmed using single-crystal X-ray analyses.

Key words: arylamines, synthesis, Caryl—N coupling, HDDA reaction