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Multicomponent Synthesis of 3,6-Dihydro-2H-1,3-thiazine-2-thiones
Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines and Systems, VU University, De Boelelaan 1083, 1081HV Amsterdam, The Netherlands
School of Chemistry, University of Manchester, Brunswick Street, Manchester, M13 9PL, UK
* Author to whom correspondence should be addressed.
Received: 5 January 2012; in revised form: 20 January 2012 / Accepted: 29 January 2012 / Published: 8 February 2012
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
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Kruithof, A.; Ploeger, M.L.; Janssen, E.; Helliwell, M.; Kanter, F.J.J.; Ruijter, E.; Orru, R.V.A. Multicomponent Synthesis of 3,6-Dihydro-2H-1,3-thiazine-2-thiones. Molecules 2012, 17, 1675-1685.
Kruithof A, Ploeger ML, Janssen E, Helliwell M, Kanter FJJ, Ruijter E, Orru RVA. Multicomponent Synthesis of 3,6-Dihydro-2H-1,3-thiazine-2-thiones. Molecules. 2012; 17(2):1675-1685.
Kruithof, Art; Ploeger, Marten L.; Janssen, Elwin; Helliwell, Madeleine; Kanter, Frans J. J. de; Ruijter, Eelco; Orru, Romano V. A. 2012. "Multicomponent Synthesis of 3,6-Dihydro-2H-1,3-thiazine-2-thiones." Molecules 17, no. 2: 1675-1685.