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Synthesis nad photochemistry of conjugated 2- and 5-oxazole derivatives

One of the most complex branches of organic chemistry is the chemistry of heterocyclic compounds [1]. Oxazoles as five membered ring aromatic compounds containing two heteroatoms are extremely interesting due to their biological activity [2]. In some of the previous research new formyl oxazole derivatives were synthesized for the first time as starting material for the building of conjugated systems [3]. We focused on the synthesis of 1-(4-methyl-2-oxazolyl)-2-(o-vinylfenyl)ethene (1) to explore its photoreactivity that appears to be completely different from the photobehaviour of previously studied 1-(4-methyl-5-oxazolyl)-2-(o-vinylfenyl)ethene (2). The starting compound (1) was prepared by Wittig reaction from 4-methyl-2-carboxaldehyde which was synthesized using a process of formylation with n-BuLi [4]. The structure determination of products gained through photochemistry of the above compounds as well as the reaction mechanism will be discussed.

photochemistry; oxazoles; intramolecular reactions; photocycloadditions

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