Trifluoroacetic Acid–Catalyzed Synthesis of N-(1-(3-Chlorophenyl)-3-aryl-3-oxopropyl)-2-(4-nitrophenyl)acetamides via Dakin–West Reaction

Author： Tian Hui-Hui   Fan Li   Zhang Xing-Hua   Zhou Cheng-He   Zhou Guang-Ming   Yang Da-Cheng  

Publisher： Taylor & Francis Ltd

ISSN： 0039-7911

Source： Synthetic Communications, Vol.44, Iss.2, 2014-01, pp. : 170-180

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Abstract

A series of novel N-(1-(3-chlorophenyl)-3-aryl-3-oxopropyl)-2-(4-nitrophenyl) acetamides were synthesized using p-nitrophenylacetonitrile, m-chlorobenzaldehyde, and aryl methyl ketones as starting materials and trifluoroacetic acid (TFA) as catalyst. This realized an improved Dakin–West reaction in which p-nitrophenylacetonitrile was involved. The chemical structures of up to 15 target molecules were characterized by 1H NMR, 13C NMR, and high-resolution mass spectrometry. This method provides a facile synthetic protocol under more moderate reaction conditions, smaller dosage (0.40 mol%) and hence lower cost of catalyst, and simpler posttreatment in comparison to other known methods. A reaction mechanism is proposed in which hydroxyacetophenone is first catalytically converted into the corresponding acetoxyacetophenone prior to be involved in the subsequent Dakin–West reaction that eventually leads to hydroxyl-acetylated target compounds.[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]

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