Microwave assisted synthesis of unsaturated jasmone heterocyclic analogues as new fragrant substances

Taking the rising interest in jasmone structure based fragrant compounds into account it has been decided to take up an attempt to synthesize the new heterocyclic derivatives of this 2,3-disubstituted cyclopentenone, which could be characterized by the ability of interaction with the same receptors with which jasmone affects. Obtained structures of unsaturated heterocyclic derivatives are based on pyrrolidinone, oxazolidinone, pyrazolidinone, pyrazolone and thiazolidinone systems with 2-double or 2-triple unsaturated five-carbon side chain. The rapid, highly yielding and ecofriendly microwave assisted organic syntheses (MAOS) have been used to obtain compounds mentioned above. Odor evaluation and relationships between their structure and osmic properties for all synthesized fragrant compounds have been studied. It has been shown that the majority of the obtained compounds have exhibited interesting, very intensive and fixative fragrant properties.

Graphical abstractThe microwave assisted synthesis of new series of heterocyclic jasmone analogues such as pyrrolidinones, oxazolidinones, pyrazolidinones, pyrazolones and thiazolidinones with unsaturated moiety in the alkyl side chain and their odor evaluation are presented.Figure optionsDownload full-size imageDownload as PowerPoint slide