5327-10-6

Usage

InChI:InChI=1/C5H9NOS2.C4H9NO/c8-5(9)6-1-3-7-4-2-6;1-3-6-4-2-5-1/h1-4H2,(H,8,9);5H,1-4H2

Upstream product

• 86202-86-0 Sb(morpholinedithiocarbamate)3 
• 110-91-8 morpholine 
• 137-26-8 Thiram 
• 729-46-4 4,4'-(dithiodicarbonothioyl)dimorpholine 
• 75-15-0 carbon disulfide 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 188290-36-0 thiophene 

Downstream Products

• 135275-10-4 4-bromophenacyl morpholine-4-carbodithioate 
• 28249-25-4 benzylmorpholine‐4‐carbodithioate 
• 26879-88-9 Ph3Sn(morpholine-1-carbodithioate) 
• 1391998-50-7 C₁₇H₂₁N₃O₄S₄ 
• 1391998-40-5 C₁₇H₂₁N₃O₄S₄ 
• 61998-15-0 S-(3-(2-hydroxyphenyl)-3-oxopropyl) morpholine-4-carbodithioate 
• 24372-61-0 2-oxo-2-phenylethyl morpholine-4-carbodithioate 
• 76539-87-2 5-Methyl-4-morpholin-4-yl-6-phenyl-5,6-dihydro-thiopyran-2-thione 
• 76539-74-7 4-Morpholin-4-yl-6-phenyl-5,6-dihydro-thiopyran-2-thione 
• 76539-72-5 (RS)-(+/-)-4-dimethylamino-6-phenyl-5,6-dihydro-2H-thiopyran-2-thione 
• 729-46-4 4,4'-(dithiodicarbonothioyl)dimorpholine 
• 62911-19-7 2-(morpholine-4-carbothioyldisulfanyl)-benzoic acid 
• 62911-22-2 p-tolyl morpholine-4-carbo(dithioperoxo)thioate 

Relevant academic research and scientific papers

New mononuclear diorganotin(IV) dithiocarboxylates: Synthesis, characterization and study of their cytotoxic activities

Since organotin complexes have been reported to show fewer side effects relative to other heavy metal anticancer compounds, in the present study we report for the first time four novel organotin(IV) derivatives with the general formula R2SnL2, where R=methyl (1), n-butyl (2), phenyl (3), benzyl (4) and L=morpholine-1-carbodithioate (MCDT). The newly synthesized ligand was monodentate or bidentate, coordinating through a sulfur atom. The complexes were synthesized by directly mixing, refluxing and stirring the ligand, with diorganotin(IV) dichlorides in a suitable solvent. The complexes were found to be pure and their solid and solution phase structural configuration was investigated by FT-IR, multinuclear NMR (1H, 13C, 119Sn) and mass spectrometry. Complex 2 was also studied for its thermal decomposition by thermogravimetry and differential thermal analysis. The results obtained on the basis of these techniques are in full concurrence with the proposed 1:2 (Sn:L) stoichiometry. The cytotoxic activity of the MCDT and diorganotin(IV) complexes (1-4) was tested against tumor cell lines - human cervix carcinoma HeLa and human myelogenous leukemia K562 - and normal immunocompetent cells: peripheral blood mononuclear cells PBMC. Results of bioassay demonstrated that organotin derivatives were in general more active than the anticancer drug cisplatin. Copyright 2012 John Wiley & Sons, Ltd. We report 4 novel diorganotin(IV) derivatives with general formula R2SnCl2, where R=methyl (1), butyl (2), phenyl (3), benzyl (4) and L=morpholine-1-carbodithioate. The complexes were found to be pure and their solid, solution phase and the structural configuration investigated by FT-IR, multinuclear NMR (1H, 13C, 119Sn) and mass spectrometry. The cytotoxicity of the complexes was tested against human tumor and normal blood cells. Results showed that diorganotin derivatives are in general more active than the cisplatin. Copyright

Cu-mediated one-pot three-component synthesis of 3-N-substituted 1,4,2-benzodithiazine 1,1-dioxide derivatives

A novel and efficient copper-catalyzed one-pot procedure for the synthesis of 3-N-substituted 1,4,2-benzodithiazine 1,1-dioxide derivatives from 2-halobenzenesulfonamides, amines and CS2 is described. The reaction proceeds through Ullmann-type S-arylation, intramolecular addition of NH2 with C[dbnd]S and dehydrosulfide, which provides a new and useful strategy for construction of cyclic aromatic sulfonamides.

A catalyst-free 1,4-Michael-type reaction of in situ generated ortho-quinone methides (o-QMs) with dithiocarbamic acid salts in water

Abstract: A catalyst-free conjugate addition of dithiocarbamic acid salts to in situ generated ortho-quinone methides (o-QMs) was investigated for the first time. Several dithiocarbamate derivatives of 4-hydroxycoumarine, 4-hydroxypyrone and 2-naphthol were synthesized in moderate-to-good yields in water at room temperature. Graphical abstract: [Figure not available: see fulltext.] Catalyst-free addition of dithiocarbamic acid salts to in situ generated o-QMs in water at room temperature.

Cyclic ammonium salts of dithiocarbamic acid: stable alternative reagents for the synthesis of S-alkyl carbodithioates from organyl thiocyanates in water

ABSTRACT: Carbodithioate esters are important functional organosulfur compounds widely used in diverse fields such as pharmaceuticals, agrochemicals and material sciences. Common preparative methods include reaction of alkyl halides, carbon disulfide and bases under both metal-free and metal-catalyzed conditions. However, organyl thiocyanates have not been previously explored, possibly because of their conversion to organyl disulfides under basic conditions. Here, we report an efficient and practical method for the preparation of libraries of carbodithioate esters from organyl thiocyanates by reacting with cyclic amine-based dithiocarbamic acid salts in water. The protocol is found to be applicable in general to various thiocyanates such as benzyl/aroyl methyl/cinnamyl and so on. Other notable features include no by-products such as disulfides, metal- and alkali-free, aqueous conditions, and finally easy and near-quantitative formation of cyclic amine-based dithiocarbamic acid salt as a stable alternative reagent.

An efficient one-pot method for the direct synthesis of organic disulfides from aryl/alkyl halides in the presence of CuCl using morpholin-4-ium morpholine-4-carbo-dithioate

A novel and expedient route is described for the one-pot synthesis of symmetric diaryl (dialkyl) disulfides derivatives via morpholin-4-ium morpholine-4-carbo-dithioate and aryl (alkyl) halides reactions in the presence of CuCl in an aqueous solvent system. Morpholin-4-ium morpholine-4-carbo-dithioate used as new solid, stable and easy handle sulfur Sourcage.

Ni-Catalyzed Cross-Coupling Reaction: The Direct Synthesis of Symmetrical Disulfanes from Aryl and Primary Alkyl Halides

A novel Ni-catalyzed cross-coupling reaction is introduced for the direct synthesis of diaryldisulfanes and dialkyldisulfanes from aryl halides and primary alkyl halides at normal atmospheric conditions, respectively. This one-pot and domino protocol utilizes only 10 mol% of NiCl2 as a catalyst and morpholin-4-ium morpholine-4-carbo-dithioate as a new, stable, solid, and odorless sulfurating reagent in the presence of ethylene glycol as a cosolvent and bidentate ligand in dimethyl formamide (DMF) at 130°C with good to excellent yields and relatively short time reaction.

Synthesis, spectroscopic characterization, X-ray structure, and in vitro antitumor activities of new triorganotin(IV) complexes with sulfur donor ligand

The discovery of the anticancer properties of cisplatin promoted a great deal of interest in the area of metal-based antitumor agents. With this aim, a new series of triorganotin(IV) derivatives: Ph3SnL (1), BZ 3SnL (2), where L = morpholine-1-carbodithioate (MCDT) have been synthesized by the reaction of triorganotin(IV) chlorides with the ligand-salt in the appropriate molar ratio. All the complexes have been characterized by FT-IR, 1H, 13C, and 19Sn NMR spectroscopy. In addition, the molecular structure of complex 1 was determined by single crystal X-ray diffraction study. X-ray crystallographic analysis shows that in the compound [Ph3Sn(MCDT)], the Sn ion is in a four-coordinate environment with a dithiocarbamate ligand coordinated to the tin(IV) in a monodentate fashion through the sulfur atom. Furthermore, the cytotoxic activity of the free ligand (MCDT) as well as its triorganotin(IV) complexes were tested against tumor cell lines human cervix carcinoma HeLa, human myelogenous leukemia K562 and normal immunocompetent cells, peripheral blood mononuclear cells PBMC. The cytotoxic results indicate that coupling of MCDT with R 3Sn(IV) metal center results in a complex with important biological properties and remarkable cytotoxic activity, since we observe IC50 values better to that of the antitumor drug cisplatin.

Utilization of carbon disulfide as a powerful building block for the synthesis of 2-aminobenzoxazoles

This protocol describes a novel, mild and convenient route to afford 2-aminobenzoxazoles in high yields, and represents a significant advance towards an environmentally friendly strategy. Aliphatic amines are made to react with carbon disulfide to provide intermediate dithiocarbamates (DTC), which in the presence of 2-aminophenol, subsequently undergo successive intermolecular nucleophilic attack and desulfurization to produce 2-aminobenzoxazoles within 3 h.

Investigation of the reaction of dithiocarbamic acid salts with aromatic aldehydes

A reaction of dithiocarbamic acid salts with carbonyl compounds was investigated for the first time in the presence of BF3?OEt 2. The reaction is temperature dependent and gives gem-bis(dithiocarbamates) at 35-45 °C as a molecule with high equivalents of dithiocarbamate groups. At lower temperatures (15-20 °C), the 2-iminium-1,3-dithietane is obtained as the only product. The structure of a 2-iminium-1,3-dithietane was accomplished by X-ray crystallographic analysis.

Thiocarbamoylation of amine-containing compounds 5. The mechanism of reactions of tetramethylthiuram disulfide with aliphatic amines

Thiocarbamoylation of aliphatic amines with tetramethylthiuram disulfide (TMTD) was studied. The reactions were established to proceed according to a two-stage mechanism. In the first stage, S-(thiocarbamoyl)thiohydroxylamines and dimethyl dithiocarbamates are formed. The latter exist in equilibrium with dimethyldithiocarbamic acid, which can undergo decomposition to give dimethylamine and carbon disulfide. In the second stage, several competitive transformations of these intermediates into the final products occur, viz., (1) the reactions of CS2 with primary amines on heating (70-110 deg C) yield mixed and symmetrical thioureas and the reactions of CS2 with secondary amines give symmetrical dithiocarbamates, and (2) insertion of CS2 into S-(thiocarbamoyl)thiohydroxylamines affords thiuram disulfides. Thiuram disulfides formed from primary amines decompose to give isothiocyanates, which are converted into thioureas by condensation with amines, whereas thiuram disulfides which are obtained in the reactions with secondary amines and which cannot form thioureas react with amines analogously to TMTD.