Enaminones are organic compounds that contain the N-C=C-C=O functional group. These compounds are widely used as synthetic intermediates in organic synthesis due to their versatile reactivity, acting as both nucleophiles and electrophiles. Aside from their uselessness in the development of pharmaceuticals and ligands for catalysis, enaminones form part of biologically active compounds that demonstrate anticonvulsive, anti-inflammatory, antibiotic, and antitumor activity. A number of methods have been developed for the synthesis of enaminones, but our group seeks a new method via a mechanochemical accelerated Eschenmoser coupling reaction. The Eshenmoser coupling reaction (Figure 1) couples a tertiary or secondary thioamide(1) with an alpha-halocarbonyl(2) compound to produce enaminones(3). This often requires a long reaction time, and primary thioamides are not acceptable substrates because of their ready conversion to nitriles. The mechanochemical facilitated reaction benefits from better mass and heat transfer compared to conventional heating and reactions are completed in minutes. The research in our group strives to find the best parameters for the mechanochemical accelerated Eschenmoser reaction by screening for speed times and base selection. A few examples of enaminones prepared by the optimized method is also reported.

Enaminone synthesis via mechanochemical accelerated eschenmoser coupling reaction

251st National Meeting (2016)

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