Manganese(III) Acetate-mediated Oxidative Cyclization of a-Methylstyrene and trans-Stilbene with b-Ketosulfones

Ahlem Bouhlel,Christophe Curti,Clémence Tabelé,Patrice Vanelle

doi:10.3390/molecules18044293

Abstract

A convenient microwave irradiation protocol was utilized for the synthesis of β-ketosulfones 1–5 in good yields. These sulfones reacted with alkenes through a radical oxidative cyclization mediated by Mn(OAc)3. Dihydrofurans 6–10 were obtained in moderate to good yields starting from 1,1-disubstituted alkenes. Dihydrofurans 11–15 were synthesized in moderate yields and unexpected cyclopropanes 16–19 were obtained in low yields starting from 1,2-disubstituted alkenes. This protocol offers access to various dihydrofurans which could be tested for their antiparasitic potential.

Highlights

Manganese(III) acetate has received considerable attention over the past several decades, and remains a useful tool for carbon-carbon bond formation [1,2,3,4]
Its specificity for carbonyl derivatives allows a wide variety of radical synthetic applications, leading to various structures like pyrrolidinones [5]
Within our research program directed towards the development of original synthesis methods in medicinal chemistry [13,14,15,16,17], we have explored the radical cyclization of -ketosulfones [18,19] mediated by manganese(III) acetate in order to synthesize dihydrofurans as potential antiparasitic compounds

Summary

Introduction

Manganese(III) acetate has received considerable attention over the past several decades, and remains a useful tool for carbon-carbon bond formation [1,2,3,4]. Its specificity for carbonyl derivatives allows a wide variety of radical synthetic applications, leading to various structures like pyrrolidinones [5],. Within our research program directed towards the development of original synthesis methods in medicinal chemistry [13,14,15,16,17], we have explored the radical cyclization of -ketosulfones [18,19] mediated by manganese(III) acetate in order to synthesize dihydrofurans as potential antiparasitic compounds. Dihydrofuran derivatives are known to have other useful pharmacological properties, such as antibacterial [20,21,22], antifungal [20,21] and anticancer activity [23], as well as being valuable potential intermediates in the synthesis of various substances [24].

Methods

Results

Conclusion