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.
Pawełczyk
Anna
A
Department of Organic Chemistry, Poznan University of Medical Sciences, Poznań, Poland. apaw@ump.edu.pl
Zaprutko
Lucjusz
L
D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006358:Hot Temperature; D007700:Kinetics; D008872:Microwaves; D009812:Odorants / Q000032:analysis; D054883:Oxylipins / Q000138:chemical synthesis* / Q000737:chemistry; D010476:Perfume / Q000138:chemical synthesis* / Q000737:chemistry
D003517:Cyclopentanes; D006571:Heterocyclic Compounds; D054883:Oxylipins; D010476:Perfume; C086299:jasmone