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Piperidone (also known as piperidinone or azinanone) is a saturated heterocyclic organic compound containing one nitrogen atom, and a carbonyl group in the ring. It exists in different isomeric forms, such as 2-piperidone, 3-piperidone and 4-piperidone. The Petrenko-Kritschenko piperidone synthesis is one of the main named reactions for the preparation of piperidone derivatives, which involves the reaction of alkyl-1,3-acetonedicarboxylate with benzaldehyde and an amine.
Piperidone-based compounds have received much attention for drug discovery research. Owing to the presence of a carbonyl group and a secondary amine group, both containing alpha-protons, the piperidone structure is a versatile moiety and finds wide applications in synthetic organic chemistry and medicinal chemistry. Piperidone-derived imines and enamines play an important role in several synthetic transformations (Kuznetzov, K. V., gamma-Piperidone imines and enamines in organic synthesis, Chemistry of Heterocyclic Compounds 1993, 30(1), 1-13). Besides the interesting structural features, these compounds are also of pharmaceutical interest as they exhibit a wide range of biological activities. Specifically, 2-piperidones have been used both as target molecules and as intermediates in the synthesis of several piperidine derivatives. 4-Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs. Hydroxylated piperidine alkaloids also have shown a wide range of biological activities due to their ability to imitate carbohydrates in a variety of enzymatic processes.