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One-Pot Formation of 1,3,4-Oxadiazol-2(3H)‑ones and Dibenzo[c,e]azepines by Concomitant Cathodic Reduction of Diazonium Salts and Phenanthrenequinones

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posted on 2016-02-18, 20:42 authored by Belen Batanero, Fructuoso Barba, Avelino Martin
The one-pot concomitant electrochemical reduction of phenanthrenequinones (1, 2) and arenediazonium salts (3af) led to the formation of 1,3,4-oxadiazol-2­(3H)-ones (4af, 5a) and dibenzo­[c,e]­azepines (6af) when N-methylformamide was used as the solvent. A new pathway, different from those previously described with other aprotic solvents, is proposed. The experimental data support a radical mechanism for the electrochemical process followed by an internal rearrangement to give the products.

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