Multicomponent Synthesis of 3,6-Dihydro-2H-1,3-thiazine-2-thiones

Abstract

Non-fused 3,6-dihydro-2H-1,3-thiazine-2-thiones constitute a so far rather unexplored class of compounds, with the latest report dating back more than two decades. Thiazine-2-thiones contain an endocyclic dithiocarbamate group, which is often found in pesticides, in substrates for radical chemistry and in synthetic intermediates towards thioureas and amidines. We now report the multicomponent reaction (MCR) of in situ-generated 1-azadienes with carbon disulfide. With this reaction, a one-step protocol towards the potentially interesting 3,6-dihydro-2H-1,3-thiazine-2-thiones was established and a small library was synthesized.

Keywords

• 3,6-dihydro-2H-1,3-thiazine-2-thiones
• cyclic dithiocarbamates
• multi-component reactions
• molecular complexity
• carbon disulfide
• 1-azadiene