Selective conversion of thioamides and thioureas to their oxygen analogues using quinolinium fluorochromate

Abstract

The synthetic utility of quinolinium fluorochromate (QFC) in deprotection of thiocarbonyl compounds is reported. A variety of primary and secondary thioamides and thioureas are converted to their oxo derivatives in high yields. However, tertiary thioamides afford their amides in relatively poor yields. Selective deprotection of thioamides and thioureas in the presence of thionoesters and thioketones is noteworthy advantage of this method.