- Cu-mediated one-pot three-component synthesis of 3-N-substituted 1,4,2-benzodithiazine 1,1-dioxide derivatives
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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.
- Dong, Wei,Ge, Zemei,Wang, Xin,Li, Ridong,Li, Runtao
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- A catalyst-free 1,4-Michael-type reaction of in situ generated ortho-quinone methides (o-QMs) with dithiocarbamic acid salts in water
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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.
- Aryanasab, Fezzeh,Shabanian, Meisam
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p. 1703 - 1713
(2019/04/17)
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- Utilization of carbon disulfide as a powerful building block for the synthesis of 2-aminobenzoxazoles
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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.
- Guntreddi, Tirumaleswararao,Allam, Bharat Kumar,Singh, Krishna Nand
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p. 9875 - 9880
(2013/09/02)
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- Thiocarbamoylation of amine-containing compounds 5. The mechanism of reactions of tetramethylthiuram disulfide with aliphatic amines
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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.
- Boi, Luu Van
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p. 335 - 343
(2007/10/03)
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- Thiocarbamoylation of amine-containing compounds 4. Reactions of tetramethylthiuram disulfide with aliphatic amines
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Thiocarbamoylation of primary and secondary aliphatic amines with tetramethylthiuram disulfide in various solvents at different temperatures was studied. At 110 °C, the reactions with primary amines afforded mixed N,N-dimethyl-N′-alkyl(cycloalkyl)thiourea
- Van Boi, Luu
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p. 2294 - 2298
(2007/10/03)
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- Standard enthalpies of formation of crystalline dimethylammoniumdimethyldithiocarbamate and of dimethyldithiocarbamate complexes of copper(II) and nickel(II). The mean Cu-S and Ni-S bond-dissociation enthalpies
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The standard (p0 = 0.1 MPa) enthalpies of formation of crystalline dimethylammoniumdimethyldithiocarbamate and of the dimethyldithiocarbamate complexes of Ni(II) and Cu(II) were determined, at the temperature 298.15 K, by solution-reaction calorimetry.The enthalpy of "decomposition" of the dimethylammoniumdimethyldithiocarbamate salt and the enthalpies of sublimation of the metal complexes were measured by high-temperature microcalorimetry.From these values, the mean molar bond-dissociation enthalpies m>(M-S) were derived. .
- Silva, Manuel A. V. Ribeiro da,Reis, Ana M. M. V.,Faria, Rita I. M. C. P.
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p. 1365 - 1372
(2007/10/02)
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