Department of Biochemistry

SynlettDOI: 10.1055/s-0040-1706409© Georg Thieme Verlag Stuttgart · New YorkArticle in Thieme eJournals:Table of contents  |  Full text

SynlettDOI: 10.1055/s-0039-1691657© Georg Thieme Verlag Stuttgart · New YorkArticle in Thieme eJournals:Table of contents  |  Full text

A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O2.

3,3-Dialkylated oxindoles (1,3-dihydro-2H-indol-2-ones), particularly those containing C3 quaternary stereogenic centers, occupy an important place in organic synthesis and drug discovery. The radical 1,2-alkylarylation of activated olefins with alkyl radicals has emerged as the most atom- and step-economical approach to 3,3-dialkylated oxindoles. This article covers important developments in the area of oxidative radical alkylation/cyclization cascade reactions of α,β-unsaturated amides toward the synthesis of alkyl-substituted oxindoles by employing a range of alkyl-radical precursors and various reaction conditions.