Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 137-143.DOI: 10.6023/cjoc201407002 Previous Articles     Next Articles



王雯, 陆秀宏, 董肖椿, 赵伟利   

  1. 复旦大学药学院 上海 201203
  • 收稿日期:2014-07-01 修回日期:2014-09-19 发布日期:2014-09-25
  • 通讯作者: 董肖椿, 赵伟利;
  • 基金资助:

    教育部博士点基金(No. 20130071110071)、上海市自然科学基金(No. 12ZR1403300)和上海市科技支撑(No. 13431900102)资助项目.

Synthesis of Azaspiro[3.4]octanes via [3+2] Cycloaddition

Wang Wen, Lu Xiuhong, Dong Xiaochun, Zhao Weili   

  1. School of Pharmacy, Fudan University, Shanghai 201203
  • Received:2014-07-01 Revised:2014-09-19 Published:2014-09-25
  • Supported by:

    Project supported by the Specialized Research Fund for the Doctoral Program of Higher Education of China (No. 20130071110071), the Shanghai Municipal Natural Science Foundation (No. 12ZR1403300), the Shanghai Municipal Science & Technology Pillar Program for Bio-pharmaceuticals (No. 13431900102).

Piperazine and morpholine are common modules in drugs. Design and synthesis of their surrogates may help to explore the chemical and patent space in medicinal chemistry. In this article, through [3+2] cycloaddition, the improved synthesis of 6-benzyl-2,6-diazaspiro[3.4]octane oxalate and 2-oxa-6-azaspiro[3.4]octane as substitutes of piperazine and morpholine was provided, respectively. Multi-gram quantities of the compounds could be easily obtained in relatively high yields.

Key words: 2,6-diazaspiro[3,4]octane, 2-oxa-6-azaspiro[3,4]octane, [3+2] cycloaddition