3-Sulfolenes and Their Derivatives: Synthesis and Applications

Abstract

The diverse substitution patterns available to 3-sulfolenes have long made them useful for the preparation of multi-substituted 1,3-diene equivalents. More recently, the 3-sulfolene motif itself (or its reduced sulfolane congener) is finding increasing application as a structural element in the creation of molecules for biological applications. This review describes various methods to afford 3-sulfolene building blocks and their derivatives. Selected applications in synthetic and medicinal chemistry are also discussed.

1 Introduction

2 The Preparation of Monocyclic Sulfolene Building Blocks

2.1 Sulfolenes through Electrophilic Addition

2.1.1 Sulfolenes through Nucleophilic Addition to 4-Bromo-2-sulfolene

2.2 Sulfolenes through Oxidation of a Thiol Precursor

2.3 Sulfolenes through Noble Metal Catalysis

2.4 Sulfolenes through Deprotonation Followed by Alkylation

3 Synthesis of Bicyclic Sulfolenes and Their Derivatives

3.1 Bicyclic Sulfolenes through Alkylation Chemistry

3.2 Heteroaromatic Bicyclic Sulfolenes

3.3 Bicyclic Sulfolenes through Dipolar Cycloaddition

4 The Sulfolane Function in Medicinal Chemistry

5 Conclusion

Key words

3-sulfolenes - 2-sulfolenes - sulfolanes - 1,3-butadiene equivalents - bicyclic sulfones - biological applications

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