Tandem Radical Cyclization of N-Arylacrylamides: An Emerging Platform for the Construction of 3,3-Disubstituted Oxindoles

Abstract

3,3-Disubstituted oxindoles are an important family of biologically active heterocycles, and numerous synthetic methodologies have been developed for their synthesis over past decades. Recently, the tandem radical cyclization of N-arylacrylamides has provided a new powerful approach to access various diversely functionalized 3,3-disubstituted oxindoles. This review will highlight recent advances in this field as well as applications in natural product synthesis in terms of different types of radical source. Particular emphases have also been placed on working models.

1 Introduction

2 Tandem Radical Addition/Cyclization Reaction of N-Arylacrylamides with Carbon Radicals

2.1 Aryl Radicals

2.2 Alkyl Radicals

2.3 Fluorine-Containing Carbon Radicals

2.4 Acyl Radicals

3 Tandem Radical Addition/Cyclization Reaction of N-Arylacrylamides with Heteroatom Radicals

3.1 Phosphonyl Radicals

3.2 Sulfur Radicals

3.3 Nitrogen Radicals

4 Conclusion and Perspective

Key words

N-arylacrylamides - heterocycles - oxindoles - radical cyclizations - tandem reactions

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