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.
A Facile Conversion of Amides and Lactams to Thioamides and Thiolactams using Tetrathiomolybdate
Ilankumaran, Palanichamy,Ramesha, A. R.,Chandrasekaran, Srinivasan
, p. 8311 - 8314 (1995)
Chloro iminium salts generated in situ from amides and lactams using (COCl)2 or POCl3 reacted very readily with the new sulfur transfer reagent, benzyltriethylammonium tetrathiomolybdate to afford the corresponding thioamides and thiolactams in excellent yields under mild reaction conditions.
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.
A new application of rhodanine as a green sulfur transferring agent for a clean functional group interconversion of amide to thioamide using reusable MCM-41 mesoporous silica
Ray, Suman,Bhaumik, Asim,Dutta, Arghya,Butcher, Ray J.,Mukhopadhyay, Chhanda
, p. 2164 - 2170 (2013/05/08)
A novel thionation protocol for amide compounds, with the system rhodanine/secondary amine has been discovered. Clean and efficient synthesis of a variety of thioamides can be achieved through this simple and convenient method using MCM-41 mesoporous silica as an acid catalyst. For this purpose we have synthesized MCM-41 silica and characterized by using an array of sophisticated analytical techniques like BET, HR TEM, EDX, XRD, 29Si MAS NMR and FTIR. This reaction is therefore a very neat example of a functional group interconversion.
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.
Thionation of amides using a solid-supported P2S5 reagent under microwave irradiation
Lagiakos, Helen Rachel,Walker, Ashley,Aguilar, Marie-Isabel,Perlmutter, Patrick
experimental part, p. 5131 - 5132 (2011/10/12)
In this Letter, we describe an improved method for the thionation of amides. Using a solid-supported P2S5 reagent, heating under microwave irradiation furnished thioamides in good to excellent yields, with a significantly reduced reaction time compared with that achieved under conventional heating. Furthermore, a change of solvent from that described in the literature enabled a simplified work-up and purification of the products.
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
Expeditious microwave-assisted thionation with the system PSCl 3/H2O/Et3N under solvent-free condition
Pathak, Uma,Pandey, Lokesh Kumar,Tank, Rekha
, p. 2890 - 2893 (2008/09/19)
(Chemical Equation Presented) A novel thionation protocol for carbonyl compounds, with the system PSCl3/H2O/Et3N has been discovered. Clean, rapid, and efficient synthesis of a variety of thiocarbonyl compounds such as thioamides, thiolactams, thioketones, thioxanthones, and thioacridone can be achieved through this simple and convenient method under solventless condition with microwave irradiation.
Synthesis and application of a fluorous Lawesson's reagent: Convenient chromatography-free product purification
Kaleta, Zoltan,Tarkanyi, Gabor,Goemoery, Agnes,Kalman, Ferenc,Nagy, Tamas,Soos, Tibor
, p. 1093 - 1095 (2007/10/03)
A fluorous analogue of Lawesson's reagent for thionation of carbonyl compounds has been developed and its use demonstrated on a series of amides, esters, and ketones. The separation of the Lawesson's reagent-derived byproducts can be achieved by a simple fluorous solid-phase extraction.
Synthesis of ω-aminodithioesters
Lacroix, Simon,Rixhon, Vinciane,Marchand-Brynaert, Jacqueline
, p. 2327 - 2334 (2008/02/03)
ω-Aminodithioester derivatives were obtained from thionolactams by reaction with an alkyl triflate followed by thiolysis with hydrogen sulfide. The presence of an electron-withdrawing group was required on the N1 position (p-nitrophenyl or benzoyl) to favor the ring opening of γ-, δ- and ε-thionolactams. In the case of β-thionolactam, activation was provided by a CF2 motif in C3 position. Georg Thieme Verlag Stuttgart.
