Chemical Research in Chinese Universities ›› 2009, Vol. 25 ›› Issue (4): 465-473.

• Articles • Previous Articles     Next Articles

Synthesis of Novel 1-Alkyl-2-chloro(alkoxy)-1H-indole 3-Carbaldehyde Oximes and Oxime-ethers(esters) Derivatives

GAO Wen-tao*, GAO De-peng and GUO Hui   

  1. Institute of Superfine Chemicals, Bohai University, Jinzhou 121000, P. R. China
  • Received:2008-05-26 Revised:2008-06-29 Online:2009-07-25 Published:2009-10-16
  • Contact: GAO Wen-tao. E-mail: isfc@bhu.edu.cn
  • Supported by:

    Supported by the Natural Science Foundation of Liaoning Province, China(No.202142037).

Abstract:

A convenient synthesis of 1-alkyl-2-chloro-1H-indole-3-carbaldehyde oximes(5a―5d) and 1-alkyl-2- phenoxy-1H-indole-3-carbaldehyde oximes(6a―6d) from 2-indolone was completed via the Vilsmeier-Haack reaction, with N-alkylation and oximation as the key steps. An improved one-pot method for the synthesis of 1-alkyl-2-alkoxy-1H-indole-3-carbaldehyde oximes(7a―7h) from 1-alkyl-2-chloro-1H-indole-3-carbaldehydes(3a―3d) was described. The Williamson reactions and esterification reactions were performed and the oxime-ethers and oxime-esters were synthesized, respectively. The new synthesized compounds(3a―11d) were characterized by  1H NMR, IR, MS, and elemental analysis.

Key words: Oxime; Indole; Vilsmeier-Haack reaction; Williamson reaction; One-pot method