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MICROWAVE-ASSISTED SYNTHESIS OF UNSATURATED HETEROCYCLIC FRAGRANT COMPOUNDS RELATED TO JASMONE

Anna Pawełczyk ,  Lucjusz Zaprutko 

Poznan University of Medical Sciences Chair and Department of Organic Chemistry, Grunwaldzka 6, Poznań 60-780, Poland

Abstract

Jasmone is well known component of plant volatiles and is very important substance which determines the odor of jasmine flowers [1]. This compound can be obtained from natural extract or by using various synthetic methods [2]. From the chemical point of view it is a 2,3-disubstituted derivative of cyclopentenone with pentenyl side chain. Natural jasmine extract contains two geometrical isomers: cis-jasmone 1 and trans-jasmone 2.

jasmony.gif

Recently we reported microwave synthesis of structural and fragrant heteroanalogues of jasmone containing saturated alkyl side chain with five-carbon atoms [3]. Saturated derivatives of pyrrolidinone, oxazolidinone and thiazolidinone have exhibited the most interesting odor and durability. The aim of the present work is preparation of successive fragrant heteroanalogues with trans-double and triple bond in the side chain.

heteroanalogi.gif

As a result of the microwave-assisted reactions the series of new jasmone heteroanalogues comprising unsaturated double or triple bond in the side chain were obtained. New fragrant compounds demonstrated an interesting, specific odor which was compared with floral, typical jasmine odor of jasmone.

References
[1] Kurek A., Zaprutko L. Pol. J. Cosmet. No 3, 140 (2004)
[2] Pawełczyk A., Zaprutko L. Wiad. Chem. 59, 509 (2005)
[3] Pawełczyk A., Zaprutko L. Eur. J. Med. Chem. in press

Acknowledgement: We are grateful for financial support to the Polish State Committee for Scientific Research (KBN Grant No 2PO5F 031 29)

 

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Submitted: 2006-01-31 07:32
Revised:   2009-06-07 00:44