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Synthesis 2016; 48(01): 1-17
DOI: 10.1055/s-0035-1560351
DOI: 10.1055/s-0035-1560351
review
3-Sulfolenes and Their Derivatives: Synthesis and Applications
Further Information
Publication History
Received: 03 July 2015
Accepted after revision: 13 August 2015
Publication Date:
05 October 2015 (online)
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
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