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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 05: 1047 - 1056

DOI: https://doi.org/10.6023/cjoc201211009

Articles

One-Pot Synthesis of N-[3-(4-Methylphenyl)-3-oxo-1-arylpropyl]ace-tamides Employing Trifluoroacetic Acid as an Efficient Catalyst

  • Ren Zhenghong ,
  • Li Sheng ,
  • Zhang Xinghua ,
  • Fan Li ,
  • Zhou Guangming ,
  • Yang Dacheng
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  • School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715

Received date: 2012-11-07

  Revised date: 2012-12-13

  Online published: 2013-01-07

Supported by

Project supported by the Chongqing Science and Technology Research Project (Nos. 2011AB5001, 2011AC1053), the National Natural Science Foundation of China (No. 21172181) and the Fundamental Research Funds for the Central Universities (No. XDJK2010C067).

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Abstract

The synthesis of a series of N-[3-(4-methylphenyl)-3-oxo-1-arylpropyl]acetamides using trifluoroacetic acid (TFA) as the catalyst was reported in this paper. It was achieved by a modified Dakin-West reaction using 4-methylacetophenone, aromatic aldehydes and acetonitrile as starting materials. The highest yield was up to 95% among the twenty eight target compounds synthesized. All the new compounds were characterized by 1H NMR, 13C NMR and HRMS spectra. This one-pot reaction offered several advantages including small catalyst loading (0.3 mol%), moderate reaction temperatures (28～35 ℃) and simple post treatment procedure. A reaction mechanism was for the first time established, in which hydroxybenzaldehyde was first catalytically converted into corresponding acetoxybenzaldehyde prior to be involved in the subsequent Dakin-West reaction that eventually led to hydroxyl acetylated target compounds. The resultant hydroxyl acetylated β-acetamido ketones were selectively deacetylated in LiOH to produce the corresponding hydroxyl products with excellent yields. The current work further demonstrated that TFA was an efficient catalyst for Dakin-West reaction involving arylalkyl ketones, aromatic aldehydes and acetonitrile, which expanded significantly the scope of the substrates and provided a new synthetic route to β-acetamido ketones.

Key words： Dakin-West reaction; multi-component reaction; trifluoroacetic acid; β-acetamido ketone; 4-methylacetophenone; aromatic aldehyde

Cite this article

Ren Zhenghong , Li Sheng , Zhang Xinghua , Fan Li , Zhou Guangming , Yang Dacheng . One-Pot Synthesis of N-[3-(4-Methylphenyl)-3-oxo-1-arylpropyl]ace-tamides Employing Trifluoroacetic Acid as an Efficient Catalyst[J]. Chinese Journal of Organic Chemistry, 2013 , 33(05) : 1047 -1056 . DOI: 10.6023/cjoc201211009

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