1480644-35-6Relevant articles and documents
Trifluoroacetic acid-catalyzed synthesis of N -(1-(3-chlorophenyl)-3-aryl- 3-oxopropyl)-2-(4-nitrophenyl)acetamides via Dakin-west reaction
Tian, Hui-Hui,Fan, Li,Zhang, Xing-Hua,Zhou, Cheng-He,Zhou, Guang-Ming,Yang, Da-Cheng
, p. 170 - 180 (2013/12/04)
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.]
