16642-93-6

3-Cyanocinnamic Acid was used to synthesize triazoles with antifungal activities. It was also used to prepare aminocyclohexylethyl-substituted methylsulfonyloxy and methylsulfonyl tetrahydrobenzazepines as dopamine receptor antagonists and antipsychotics.

GENERAL METHOD: 3-cyanobenzaldehyde (11a) or 4-cyanobenzaldehyde (11b) (15 mmol) and malonic acid (30 mmol) were dissolved in pyridine (30 mL). Piperidine (3.0 mmol) was added to the solution and the reaction mixture was subsequently heated to reflux at 100 °C for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and acidified by slow addition of 5 M hydrochloric acid solution (25 mL). The precipitated white precipitate was collected by filtration, washed well with water and dried to give the target products (E)-3-cyanocinnamic acid (12a) or (E)-4-cyanocinnamic acid (12b) in 81% and 78% yields, respectively.

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