Jasmone is well-known of natural origin ketone from jasmonoids group and is important representative of jasmine fragrant compounds, derived from polyunsaturated fatty acids as a result of biosynthesis in plants [1]. The synthesis of thioanalogues of ketones, flavones, lactones, amides and esters has received considerable attention due to biological and commercial importance of these molecules and their usefulness as precursors for the synthesis of various organic compounds. The common procedures for the chemical oxygen-sulfur exchange in the carbonyl compounds require the use of dry aromatic hydrocarbon solvents, lengthy reaction times and usually excess of thionathion reagent [2].
The starting heterocyclic analogues of jasmone based on oxazolidinone, pyrrolidinone, pyrazolidinone, pyrazolinone and thiazolidinone cycles were successfully prepared under microwave irradiation [3]. In the present investigation we report a rapid, solvent free, high yielding and cleaner conversion of heteroanalogues of jasmone to the corresponding thioanalogues by using Lawesson's reagent.

Odor quality and durability of obtained jasmone hetero- and appropriate thioheteroanalogues were evaluated and compared with fragrance properties of typical floral odor of jasmone.

References
[1] Kurek A., Zaprutko L. Pol. J. Cosmet. N^o 3, 140 (2004)
[2] Varma R.S., Kumar D. Org. Lett. 1, 679 (1999)
[3] Pawełczyk A., Zaprutko L. Eur. J. Med. Chem. in press

Acknowledgements: We are grateful for financial support to the Polish State Committee for Scientific Research (KBN Grant N^o 2PO5F 031 29)

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