Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (5): 1266-1272.DOI: 10.6023/cjoc201612049 Previous Articles     Next Articles

Articles

微波辅助下高效合成功能性6-芳基水杨酸类衍生物(英文)

曲仁渝, 陈念, 刘玉超, 陈琼, 杨光富   

  1. 华中师范大学化学学院 农药与化学生物学教育部重点实验室 武汉 430079
  • 收稿日期:2016-12-19 修回日期:2017-01-15 发布日期:2017-01-20
  • 通讯作者: 杨光富 E-mail:gfyang@mail.ccnu.edu.cn
  • 基金资助:

    公益性行业(农业)科研专项经费(No.201203022)、国家科技攻关计划(No.2014BAD23B01)和国家自然科学基金(No.21372093)资助项目.

An Efficient Synthesis of Functionalized 6-Arylsubstituted Salicylates via Microwave Irradiation

Qu Renyu, Chen Nian, Liu Yuchao, Chen Qiong, Yang Guangfu   

  1. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079
  • Received:2016-12-19 Revised:2017-01-15 Published:2017-01-20
  • Contact: 10.6023/cjoc201612049 E-mail:gfyang@mail.ccnu.edu.cn
  • Supported by:

    Project supported by the Special Fund for Agroscientific Research in the Public Interest (No. 201203022), the National Key Technologies R&D Program (No. 2014BAD23B01) and the National Natural Science Foundation of China (No. 21372093).

Functionalized 6-arylsalicylate substructures occur in a variety of pharmacologically relevant natural products and bioactive compounds. Especially 6-arylsubstituted salicylates, as a key pharmacophore of anti-resistant acetohydroxyacid synthase (AHAS) inhibitors have played a lead role in combatting the weed-resistance issues. Previously, we have explored two new methods to synthesize position-6 aryl substituted salicylic acid fragment. However, these two methods failed to introduce various substituents into salicylic acid. Here an efficient method for the synthesis of 6-substituted salicylates is described via a microwave-promoted Suzuki cross-coupling. Due to the obvious advantages of this method, such as a wide range of substrates, smooth and rapid reaction and moderate to excellent yields, this protocol could be utilized to synthesize more anti-resistant AHAS inhibitors.

Key words: Functionalized 6-arylsalicylates, Suzuki cross-coupling reactions, Microwave irradiation, Electronic effect