Formation of Five- and Six-Membered Heterocyclic Rings under Radical Cyclization Conditions

Abstract

This review describes the formation of five- and six-membered heterocyces in various organic molecules by radical cyclization­ and covers the progress made on the topic during the period­ of 2008 through 2010.

1 Introduction

2 Reagents, Solvents, Radical Initiators, and Reactivity

3 General Mechanistic Pathways: Regio- and Stereoselectivity

4 Synthesis of Nitrogen Heterocycles

4.1 Nitrogen-Centered Radical Cyclizations

4.2 N-Vinylic and Related Systems

4.3 N-Allylic and Related Systems

4.4 N-Alkyl and Related Systems

4.5 Diastereoselective Radical Cyclizations

4.6 Cascade and Tandem Radical Cyclizations

4.7 Atom- and Group-Transfer Radical Cyclizations

4.8 Oxidative Radical Cyclizations

4.9 Miscellaneous

5 Synthesis of Oxygen Heterocycles

5.1 Diastereoselective Radical Cyclizations

5.2 Miscellaneous

6 Synthesis of Sulfur Heterocycles

7 Synthesis of Silicon Heterocycles

8 Miscellaneous

9 Conclusions

Key words

radical cyclization - tributyltin hydride - cascade cyclization - nitrogen heterocycles - radical relay cyclization - atom-transfer radical cyclization - tandem radical cyclization - oxidative radical cyclization

• References

• 1 Present address: Crop Protection Chemicals Division, Indian Institute of Chemical Technology, Hyderabad 500607, India.
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