Sulfur monochloride in organic synthesis

Synthesis and antiproliferative properties of a new ceramide analog of varacin

“…The synthesis of 4-nitrophenyl benzo[ f ][1,2,3,4,5]pentathiepine-7-carboxylate 9 was carried out as described before (Mahendran et al, 2010), using 3,4-dihydroxybenzoic acid ( 8 ) as a starting material, as well as the use of thiostannole and disulfur dichloride chemistry (Lienard et al 2007; Ogawa et al, 1994; Konstantinova and Rakitin, 2014) (Scheme 2). Briefly, compound 9 was synthesized in seven steps in 2.8% yield, and was reacted with D -erythro-sphingosine (0.035 mmol) in THF to form conjugate 1 .…”

1,3,5-Trithianes and sulfur monochloride/sodium sulfide: an alternative route to 3,5-disubstituted 1,2,4-trithiolanes

“…Time ago was likewise reported the synthesis of α-dihalogeno sulfides upon treatment of 1,3,5-trithianes with bromine [39]. In this connection, searching for a convenient synthetic route to trithiolanes, our attention was focused to the behavior of 1,3,5-trithianes, prepared following our reported procedure [32][33][34] which is commonly used as powerful sulfurating agent in the synthesis of heterocycles, and only rarely as chlorinating reagent [40,41]. In order to search for chlorination conditions, a first screening was performed investigating the reaction of trithiane 1a (R = Me) with S 2 Cl 2 2 under different reaction conditions (Scheme 2).…”

8-(Pyrimidin-2-yl)-1,2,3,4,5,6,7,8-heptathiazocane

“…It is known that disulfur dichloride is an important reagent in the synthesis of heterocycles with various numbers of sulfur atoms [7][8][9]. The formation of every heterocycle from S 2 Cl 2 requires precise selection of the reaction conditions-an appropriate base, solvent, and temperature, which can significantly improve the yields of the target compounds.…”