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Electrochemical synthesis of heterocyclic compounds—XVIII. Anodic oxidation of 2′-hydroxychalcones

✍ Scribed by Živko Saničanin; Ibro Tabaković

Publisher
Elsevier Science
Year
1988
Tongue
English
Weight
386 KB
Volume
33
Category
Article
ISSN
0013-4686

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✦ Synopsis

Anodic oxidations of a series of 2'-hydroxychalcones were performed in acetonitriletetraethylammonium perchlorate electrolyte solution at'a graphite felt electrode using controlled potentials. As a result of two electron oxidation several flavones (la-4a, 'fa) and flavanonols (6e) were obtained in the yields ranging from 40 to 75 %. As a result of four electron oxidation flavanol (Sa) was obtained in 60 yO yield. From the results of the dependence of the oxidability on substitution in the rings A and B for 16 structurally different 2'-hydroxychalcones, as well as from preparative results, it was proposed that the oxidation is initiated by removal of the electrone from the styrene moity. The mechanism of the anodic oxidation of 2'hydroxychalcones was discussed.

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