Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions)

Art Kruithof, Christophe Vande Velde, Eelco Ruijter, Romano Orru
2017 Molecules  
We report the unexpected formation of a 1-azadiene dimer from 4,6-diphenyl-3,6-dihydro-2H-1,3-thiazine-2-thiones under prolonged microwave irradiation. In this manner, thiazine-2-thiones act as "masked" 1-azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier approaches and elaborate on the observed diastereoselectivity. Abstract: We report the unexpected formation of a 1-azadiene dimer from
more » ... r from 4,6-diphenyl-3,6-dihydro-2H-1,3-thiazine-2-thiones under prolonged microwave irradiation. In this manner, thiazine-2thiones act as "masked" 1-azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier approaches and elaborate on the observed diastereoselectivity.
doi:10.3390/molecules22040541 pmid:28350361 fatcat:vafnygplmnhk3nbhlhcfftkbjq