Synthesis 2016; 48(03): 407-412
DOI: 10.1055/s-0035-1560964
paper
© Georg Thieme Verlag Stuttgart · New York

Cascade Oxa-Michael–Henry Reaction of Salicylaldehydes with Nitrostyrenes via Ball Milling: A Solvent-Free Synthesis of 3-Nitro-2H-chromenes

Authors

  • Shui-Xiang Liu

    a   Hainan Provincial Key Lab of Fine Chemistry (Hainan University), Haikou, Hainan 570228, P. R. of China   Email: zhangqi@hainu.edu.cn   Email: hnfinechem@163.com
  • Chun-Man Jia*

    a   Hainan Provincial Key Lab of Fine Chemistry (Hainan University), Haikou, Hainan 570228, P. R. of China   Email: zhangqi@hainu.edu.cn   Email: hnfinechem@163.com
    b   Key Study Center of the National Ministry of Education for Tropical Resources Utilization (Hainan University), Haikou, Hainan 570228, P. R. of China
  • Bo-Yuan Yao

    a   Hainan Provincial Key Lab of Fine Chemistry (Hainan University), Haikou, Hainan 570228, P. R. of China   Email: zhangqi@hainu.edu.cn   Email: hnfinechem@163.com
  • Xiang-Long Chen

    a   Hainan Provincial Key Lab of Fine Chemistry (Hainan University), Haikou, Hainan 570228, P. R. of China   Email: zhangqi@hainu.edu.cn   Email: hnfinechem@163.com
  • Qi Zhang*

    a   Hainan Provincial Key Lab of Fine Chemistry (Hainan University), Haikou, Hainan 570228, P. R. of China   Email: zhangqi@hainu.edu.cn   Email: hnfinechem@163.com
    b   Key Study Center of the National Ministry of Education for Tropical Resources Utilization (Hainan University), Haikou, Hainan 570228, P. R. of China
Further Information

Publication History

Received: 24 August 2015

Accepted after revision: 23 October 2015

Publication Date:
07 December 2015 (online)


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Abstract

Cascade oxa-Michael–Henry reactions of salicylaldehyde derivatives with β-nitrostyrenes catalyzed by potassium carbonate via solvent-free ball milling are demonstrated. The corresponding 3-nitro-2H-chromene products were obtained in moderate to excellent yields. This method offers significant advantages, particularly in terms of high yields, short reaction times and mild conditions.