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Persulfate-mediated decarboxylation of arylacetic acids is well-versed and a preferred choice for functionalization. However, certain substituted arylacetic acids do not follow the expected decarboxylation trend and may lead to other different functionalizations, which remain elusive in the literature. The effect of ortho-substitution on persulfate-mediated decarboxylation and functionalization of arylacetic acids forms the basis of this report, wherein the presence of different electron-withdrawing or electron-releasing groups exerts different effects on the fate as well as rate of decarboxylation. In so doing, the synthesis of ortho-hydroxy N-arylacetamides under persulfate-mediated one-pot conditions is developed. [ABSTRACT FROM AUTHOR]

An improved, gram-scale synthesis of the blockbuster drug sildenafil, used for the treatment of male erectile dysfunction, has been developed. Unlike the previous literature, the current method demonstrates the use of arylacetic acid as an acyl source, a cheap oxidant K2S2O8, and water as the reaction medium in the key step of pyrrazolo[4,3-d]pyrimidin-7-one ring formation. As well as being a green and benign approach, the current method reduces the cost by half compared to our previous strategy. In addition, the general relevance of the method has been demonstrated in the synthesis of a variety of quinazolinone and benzothiazole derivatives with excellent functional group tolerance. [ABSTRACT FROM AUTHOR]