Molecules 2012, 17(2), 1675-1685; doi:10.3390/molecules17021675
Communication

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

Art Kruithof 1 , Marten L. Ploeger 1 , Elwin Janssen 1 , Madeleine Helliwell 2 , Frans J. J. de Kanter 1 , Eelco Ruijter 1  and Romano V. A. Orru 1,* email
1 Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines and Systems, VU University, De Boelelaan 1083, 1081HV Amsterdam, The Netherlands 2 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
(This article belongs to the Special Issue Multicomponent Reaction)
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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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Cite This Article

MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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