Bargellini reaction

[1] The original reaction was a mixture of the reagents phenol, chloroform, and acetone in the presence of a sodium hydroxide solution.

[2] Prior to Bargellini's research, the product attributed to this multi-component reaction (MCR) had been described as a phenol derivative in chemistry texts at the time.

His interest in coumarins, a recently isolated compound at the time, led Bargellini to experiment with multi-component reactions (MCRs) between phenols, chloroform, and acetone in a solution of a sodium hydroxide.

Since Bargellini correctly identified the product, its structure and properties, then published his results in the Gazzetta Chimica Italiana, the reaction was named after him.

The amine can attack the oxirane due to formation of tertiary carbocation in a nucleophilic substitution SN1 concerted elimination of one atom of chlorine.

The nucleophilic intermediate is highly reactive and regioselective at the α-carbon, resulting in the formation of a α-substituted carboxylic acid chloride.

The final step occurs by nucleophilic acyl substitution and solvolysis, where the amino or hydroxyl group attacks the acid chloride forming the corresponding heterocycle.