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
