Electrochemical synthesis of heterocyclic compounds—XVIII. Anodic oxidation of 2′-hydroxychalcones
1988; Elsevier BV; Volume: 33; Issue: 11 Linguagem: Inglês
10.1016/0013-4686(88)80230-5
ISSN1873-3859
AutoresŽivko Saničanin, Ibro Tabaković,
Tópico(s)Electrochemical sensors and biosensors
ResumoAbstract Anodic oxidation of a series of 2′-hydroxychalcones were performed in acetonitrile—tetraethylammonium perchlorate electrolyte solution at a graphite felt electrode using controlled potentials. As a result of two electron oxidation several flovones (1a–4a, 7a) and flavanonols (6a) were obtained in the yields ranging from 40 to 75%. As a result of four electron oxidation flavanol (5a) was obtained in 60% 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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