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  • Title: Direct formation of ring-fused 1,3-thiazine-2,4-dithiones from aromatic o-amino carboxylic acids: observation of a carbon disulfide mediated thionation.
    Author: Ottersbach PA, Elsinghorst PW, Häcker HG, Gütschow M.
    Journal: Org Lett; 2010 Aug 20; 12(16):3662-5. PubMed ID: 20666472.
    Abstract:
    A facile synthesis of 2H-3,1-benzothiazine-2,4(1H)-dithiones (trithioisatoic anhydrides) or 2H-naphtho[2,3-d][1,3]thiazine-2,4(1H)-dithione solely from anthranilic acids or 3-amino-2-naphthoic acid and carbon disulfide, performed at room temperature in 1,4-dioxane in the presence of Et(3)N, is reported. Corresponding 2-alkylsulfanyl derivatives were obtained in one-pot reactions under the same conditions after addition of alkyl halides. The mechanism of the thiazine cyclization was investigated using (13)C-labeled carbon disulfide to reveal that carbon disulfide was incorporated into the heterocycle and additionally acted as a thionation reagent.
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