Multicomponent synthesis of 3,6-dihydro-2H-1,3-thiazine-2-thiones.
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.
Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines and Systems, VU University, De Boelelaan 1083, 1081HV Amsterdam, The Netherlands.
Art
A
Kruithof
Marten L
ML
Ploeger
Elwin
E
Janssen
Madeleine
M
Helliwell
Frans J J
FJ
de Kanter
Eelco
E
Ruijter
Romano V A
RV
Orru
D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry; D013871:Thiones / Q000138:chemical synthesis* / Q000737:chemistry
D013843:Thiazines; D013871:Thiones