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Article
Chemo and regioselective serendipitous electrochemically initiated spirocyclization of caffeic acid esters with barbituric acid derivatives
Electrochimica Acta
(2015)
Abstract
An interesting sequence of oxidation/Michael addition/oxidation/spirocyclization is observed in the electrolysis of caffeic acid esters in the presence of barbituric acid derivatives leading to the synthesis of a series of novel spirocycles. In an experimentally simple and clean procedure, the electrolyses proceed via a domino of electrochemical (E) and chemical (C) events with employing electrons as the only reagents in aqueous solution without introducing any catalyst or oxidant. From mechanistic point of view, a new type of domino mechanism (ECECi, Ci = spirocyclization) is proven with a unique Ci phenomenon at final step. Also, in light of experimental and theoretical NMR investigations, highly chemo and regioselectivities have been detected in these synthetic electrolyses.
Keywords
- Electrosynthesis,
- Spirocyclization,
- Caffeate esters,
- Cyclic Voltammetry,
- Barbituric acids.
Disciplines
Publication Date
August 12, 2015
DOI
10.1016/j.electacta.2015.08.014
Citation Information
Abdolhamid Alizadeh. "Chemo and regioselective serendipitous electrochemically initiated spirocyclization of caffeic acid esters with barbituric acid derivatives" Electrochimica Acta Vol. 178 (2015) p. 533 - 540 Available at: http://works.bepress.com/abdolhamid-alizadeh/13/