Pellizzari reaction

Pellizzari the reaction is a reaction of the organic chemical name. It was named after the chemist Guido Pellizzari, who published them in 1894. With the help of this reaction can be produced 1,2,4- triazole or corresponding derivatives.

Survey

Amides react in the reaction (on the left ) with hydrazides to 1,2,4- triazoles or derivatives thereof.

Mechanism

Initially, the carbon atom of the carbonyl group in the amide 1 attacked by a Stickstofffatom the hydrazide 2. 3, the hydrogen in the molecule is cleaved from the nitrogen and is a bond to the oxygen atom. Under elimination of water from the nitrogen molecule 4 forms a double bond to carbon 5 of ( formation of an imine ). The following is an intramolecular attack on the carbonyl group, resulting in the formation of a five- ring 6. After another proton migration and subsequent elimination of water arises from the 1,2,4-triazole 7 8