title: 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.
abstract: The one-pot concomitant electrochemical reduction of phenanthrenequinones (1, 2) and arenediazonium salts (3a-f) led to the formation of 1,3,4-oxadiazol-2(3H)-ones (4a-f, 5a) and dibenzo[c,e]azepines (6a-f) 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.
authors: Department of Organic Chemistry, University of Alcalá , 28871 Alcalá de Henares, Madrid, Spain.
authors: Belen
authors: B
authors: Batanero
authors: Fructuoso
authors: F
authors: Barba
authors: Avelino
authors: A
authors: Martin
mesh_terms: D003024:Clozapine / Q000138:chemical synthesis* / Q000737:chemistry; D003979:Diazonium Compounds / Q000737:chemistry*; D004566:Electrodes; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010616:Phenanthrenes / Q000737:chemistry*; D012492:Salts / Q000737:chemistry
chemical_list: C586624:1,3,4-oxadiazol-2(3H)-one; D003979:Diazonium Compounds; D010069:Oxadiazoles; D010616:Phenanthrenes; D012492:Salts; C586625:dibenzo(c,e)azepine; C005399:9,10-phenanthrenequinone; D003024:Clozapine