Synthesis 2015; 47(05): 604-629
DOI: 10.1055/s-0034-1378944
short review
© Georg Thieme Verlag Stuttgart · New York

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

Jia-Rong Chen*a, b, Xiao-Ye Yua, b, Wen-Jing Xiao*a, b
  • aKey Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China   Email: chenjiarong@mail.ccnu.edu.cn   Email: wxiao@mail.ccnu.edu.cn
  • bCollaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, P. R. of China
Further Information

Publication History

Received: 13 October 2014

Accepted after revision: 05 November 2014

Publication Date:
05 December 2014 (eFirst)

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