Vinylation of N-Heteroarenes through Addition/Elimination Reactions of Vinyl Selenones

Author:

Palomba Martina1,Dias Italo Franco Coelho1,Cocchioni Michelangelo1,Marini Francesca1ORCID,Santi Claudio1ORCID,Bagnoli Luana1ORCID

Affiliation:

1. Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo, 1, 06123 Perugia, Italy

Abstract

A new protocol for the synthesis of N-vinyl azoles using vinyl selenones and azoles in the presence of potassium hydroxide was developed. This reaction proceeded under mild and transition metal-free conditions through an addition/elimination cascade process. Both aromatic and aliphatic vinyl selenones and various mono-, bi- and tri-cyclic azoles can be tolerated and give terminal N-vinyl azoles in moderate to high yields. A plausible mechanism is also proposed.

Funder

University of Perugia “Fondo per la Ricerca di Base”

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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