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An efficient electrochemical method for a unique synthesis of new derivatives of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one
Authors:L Fotouhi  D Nematollahi  MM Heravi
Institution:a Department of Chemistry, Faculty of Sciences, Al-Zahra University, PO Box 1993891167, Tehran, Iran
b Department of Chemistry, Faculty of Sciences, Bu-Ali-Sina University, PO Box 65174, Hamadan, Iran
Abstract:The electrochemical oxidation of catechols (1a-c) has been studied in the presence of 6-methyl-1,2,4-triazine-3-thion-5-one 3 in aqueous sodium acetate, using cyclic voltammetry and controlled-potential coulometry. A plausible mechanism for the oxidation of catechols and their reaction with 3 is presented. All the catechol derivatives (1a-c) were converted into 7H-thiazolo3,2-b]-1,2,4-triazin-7-one derivatives (6a-c) through a Michael-type addition reaction of 3 to anodically generated o-quinones. The electrochemical syntheses of 6a-c were successfully performed in one pot in an undivided cell using an environmentally friendly method with high atomic economy.
Keywords:Electrochemical oxidation  Michael-type addition  Quinone  6-Methyl-1  2  4-triazine-3-thion-5-one  7H-Thiazolo[3  2-b]-1  2  4-triazin-7-one
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