Electrochemical generation of phenothiazin-5-ium. A sustainable strategy for the synthesis of new bis(phenylsulfonyl)-10H-phenothiazine derivatives

Niloofar Mohamadighader; Faezeh Zivari-Moshfegh; Davood Nematollahi

doi:10.1038/s41598-024-53620-0

Electrochemical generation of phenothiazin-5-ium. A sustainable strategy for the synthesis of new bis(phenylsulfonyl)-10H-phenothiazine derivatives

Sci Rep. 2024 Feb 21;14(1):4276. doi: 10.1038/s41598-024-53620-0.

Authors

Niloofar Mohamadighader¹, Faezeh Zivari-Moshfegh¹, Davood Nematollahi²

Affiliations

¹ Faculty of Chemistry and Petroleum Sciences, Bu-Ali-Sina University, Hamedan, 65174-38683, Iran.
² Faculty of Chemistry and Petroleum Sciences, Bu-Ali-Sina University, Hamedan, 65174-38683, Iran. nemat@basu.ac.ir.

Abstract

In this work, the electrochemical generation of phenothiazin-5-ium (PTZ_ox) from the direct oxidation of phenothiazine (PTZ) in a water/acetonitrile mixture using a commercial carbon anode and conventional stainless steel cathode is reported. PTZ_ox is a reactive intermediate with high potential synthetic applications, which is used in this paper for the synthesis of new phenothiazine derivatives. In this work a novel and simple electrochemical methodology for the synthesis of some bis(phenylsulfonyl)-10H-phenothiazine derivatives was established. In this paper, a mechanism for PTZ oxidation in the presence of arylsulfinic acids has been proposed based on the results obtained from voltammetric and coulometric experiments as well as spectroscopic data of the products. These syntheses are performed in a simple cell by applying constant current under mild conditions and at room temperature with high atom economy.