Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (1): 126-136.DOI: 10.6023/cjoc201307020 Previous Articles     Next Articles

Articles

卤素功能化靛红的合成及其烃基化、还原和酰基化反应研究

高文涛, 赵鹏波, 赵宾宾, 李阳   

  1. 渤海大学超精细化学品研究所 锦州 121000
  • 收稿日期:2013-07-14 修回日期:2013-09-14 出版日期:2014-01-25 发布日期:2014-09-30
  • 通讯作者: 高文涛 E-mail: isfc@bhu.edu.cn
  • 基金资助:

    辽宁省自然科学基金(No. 20120001)资助项目.

Synthesis, Alkylation, Reduction and Acylation of Halo-functionalized Isatins

Gao Wentao, Zhao Pengbo, Zhao Binbin, Li Yang   

  1. Institute of Superfine Chemicals, Bohai University, Jinzhou 121000
  • Received:2013-07-14 Revised:2013-09-14 Online:2014-01-25 Published:2014-09-30
  • Supported by:

    Project supported by the Natural Science Foundation of Liaoning Province (No. 20120201).

In this paper, 4-haloanilines were first underwent the Sandmeyer reaction to give the corresponding halo-functionalized isatins 3a3c, which were further alkylated at the nitrogen atom to give 4a4o followed by in situ reduction using hydrazine hydrate to obtain the oxindole products 5a5o. 5a5o were subjected to the acetylation reaction by the treatment with acetic anhydride in the presence of a catalytic amount of N,N-dimethylaminopyridine to afford the intermediates of 2-acetoxy-3-acetylindoles, which were used in next step without further purifucation. Subsequently, the hydrolysis reaction of the arising ester functions of the intermediates was carried out in tetrahydrofuran (THF) with the presence of 5% aq. NaOH at room temperature to give the targeted compounds 6a6o. Some compounds synthesized are novel. Their structures were confirmed by 1H NMR, 13C NMR, IR, MS and elemental analysis.

Key words: halo-functionalized isatin, reduction, alkylation, acetylation