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

K. C. Majumdar; Galla V. Karunakar; Biswajit Sinha

doi:10.1055/s-0032-1316566

Synthesis, Table of Contents

Synthesis 2012; 44(16): 2475-2505
DOI: 10.1055/s-0032-1316566

review

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

K. C. Majumdar*

^aDepartment of Chemical Sciences, Tezpur University, Napaam, Tezpur 784024, Assam, India

^bDepartment of Chemistry, University of Kalyani, Kalyani 741235, India, Fax: +91(33)25827521 Email: kcm@klyuniv.ac.in

,

Galla V. Karunakar

^aDepartment of Chemical Sciences, Tezpur University, Napaam, Tezpur 784024, Assam, India

,

Biswajit Sinha

^bDepartment of Chemistry, University of Kalyani, Kalyani 741235, India, Fax: +91(33)25827521 Email: kcm@klyuniv.ac.in

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Abstract

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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

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References

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