Cyanide is a useful one-carbon nucleophile that participates in substitution and conjugate addition reactions. Conjugate hydrocyanation reactions of α,β-unsaturated carboxylic acid derivatives and ketones have known since the 1970s. Since then, there have been studies exploring this reaction mechanism on α,β-unsaturated aldehydes. The research explores the synthesis of β-cyanoamides due to cyanide’s unreactivity with α,β-unsaturated amides. Therefore, the synthesis approach involves sequential 1,4- and 1,2-additions of cyanide to an α,β-unsaturated aldehyde starting material, followed by oxidation of the intermediate cyanohydrin to an acyl cyanide and displacement with an amine, to provide the target β-cyanoamide. Current efforts have focused on optimizing the first step of the process, which is the double cyanide addition reaction. Different solvents and reaction acids have been explored in various ratios to optimize reaction yield and purity. The reactions were performed in parallel on small scale (~0.2 mmol) and analyzed through GC-MS. Initial results from the second oxidation-displacement step will be reported, as well.

Investigations into the conjugate hydrocyanation of α,β-unsaturated aldehydes in organic synthesis

255th National Meeting (2018)

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