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Visible-light-promoted sulfenylation of 6-aminouracils under catalyst-free conditions†
B. Shriya Saikia,Paran J. Borpatra,Iftakur Rahman,Mohit L. Deb,Pranjal K. Baruah
New Journal of Chemistry Pub Date : 08/15/2022 00:00:00 , DOI:10.1039/D2NJ01941H
Abstract

Visible-light-promoted reactions have proven to be a decent strategy for the synthesis of complex molecules. Here, we report a catalyst-free method for the sulfenylation of 6-aminouracils which uses visible light as a source of clean and eco-energy. Uracils are pyrimidine derivatives and many of them are biologically potent. When 6-aminouracil and its derivatives are reacted with different thiols under the irradiation of a compact fluorescent light (CFL, 20 W) in dimethyl sulfoxide solvent in an open reaction vessel at room temperature, sulfenylation takes place at the 5-position of 6-aminouracils and forms a new C–S bond. The products are obtained in 59–94% yields. This photochemical transformation without using any catalyst makes the method even more valuable. A wide range of 6-aminouracil substrates are well tolerated for the sulfenylation. The disulfide, a potential therapeutic, can also be synthesized under these conditions which is an added advantage of the method.

Graphical abstract: Visible-light-promoted sulfenylation of 6-aminouracils under catalyst-free conditions
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