Issue 34, 2022

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

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

Supplementary files

Article information

Article type
Paper
Submitted
20 Apr 2022
Accepted
03 Aug 2022
First published
15 Aug 2022

New J. Chem., 2022,46, 16523-16529

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

B. S. Saikia, P. J. Borpatra, I. Rahman, M. L. Deb and P. K. Baruah, New J. Chem., 2022, 46, 16523 DOI: 10.1039/D2NJ01941H

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