10441-57-3Relevant articles and documents
Conversion of Amides and Lactams to Thioamides and Thiolactams Using Hexamethyldisilathiane
Smith, D. C.,Lee, S. W.,Fuchs, P. L.
, p. 348 - 354 (1994)
Amides and lactams were converted to their corresponding thioamides and thiolactams employing a new protocol using hexamethyldisilathiane (TMS2S).Oxophilic promoters were employed to generate Vilsmeier-type intermediates, the most efficient reagents being phosphorus oxychloride, triphosgene, and oxalyl chloride.Thionation of intermediate chloro iminium ions was accomplished in situ with TMS2S.Yields were good to excellent for secondary and tertiary amides and lactams while yields for primary systems were poor.
Modification of organic compounds with Lawesson's reagent
Kayukova,Praliyev,Gut'Yar,Baitursynova
, p. 148 - 160 (2015/04/14)
Application in organic synthesis of Lawesson's reagent, 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, provides a possibility to replace an oxygen atom for a sulfur atom in the carbonyl group of ketones, esters, amides, in ether group, and also either to induce a rearrangement of the initial structure of organic compounds with or without inclusion of sulfur atoms or to lead to the formation of various types of organophosphorus compounds. The formed organosulfur compounds exhibit a wide range of biological action.
Ruthenium catalyzed synthesis of enaminones
Koduri, Naga Durgarao,Scott, Halee,Hileman, Bethany,Cox, Justin D.,Coffin, Michael,Glicksberg, Lindsay,Hussaini, Syed R.
supporting information; experimental part, p. 440 - 443 (2012/03/10)
The Grubbs first-generation catalyst has been found to be an effective catalyst for the synthesis of enaminones by coupling thioamides with α-diazodicarbonyl compounds. The reaction is successful in converting primary, secondary, and tertiary thioamides into their corresponding enaminones. The reaction is also suitable for the synthesis of chiral enaminones.
Reaction of optically active oxiranes with thiofenchone and 1-methylpyrrolidine-2-thione: Formation of 1,3-oxathiolanes and thiiranes
Fu, Changchun,Linden, Anthony,Heimgartner, Heinz
experimental part, p. 773 - 784 (2011/06/27)
The SnCl4-catalyzed reaction of (-)-thiofenchone (=1,3,3-trimethylbicyclo[2.2.1]heptane-2-thione; 10) with (R)-2-phenyloxirane ((R)-11) in anhydrous CH2Cl2 at -60° led to two spirocyclic, stereoisomeric 4-phenyl-1,3-oxathiolanes 12 and 13 via a regioselective ring enlargement, in accordance with previously reported reactions of oxiranes with thioketones (Scheme 3). The structure and configuration of the major isomer 12 were determined by X-ray crystallography. On the other hand, the reaction of 1-methylpyrrolidine-2-thione (14a) with (R)-11 yielded stereoselectively (S)-2-phenylthiirane ((S)-15) in 56% yield and 87-93% ee, together with 1-methylpyrrolidin-2-one (14b). This transformation occurs via an SN2-type attack of the S-atom at C(2) of the aryl-substituted oxirane and, therefore, with inversion of the configuration (Scheme 4). The analogous reaction of 14a with (R)-2-{[(triphenylmethyl)oxy] methyl}oxirane ((R)-16b) led to the corresponding (R)-configured thiirane (R)-17b (Scheme 5); its structure and configuration were also determined by X-ray crystallography. A mechanism via initial ring opening by attack at C(3) of the alkyl-substituted oxirane, with retention of the configuration, and subsequent decomposition of the formed 1,3-oxathiolane with inversion of the configuration is proposed (Scheme 5). Copyright
