76697-38-6Relevant articles and documents
Primary sulfonamide as a coupling partner: Copper(I)-catalyzed regioselective cross-coupling of 2-nitro benzenesulfonamides with thiol through the cleavage of Ar–SO2NH2 bonds
Chen, Junmin,Zhang, Kuo,Zhao, Yongli,Pu, Shouzhi
, p. 1316 - 1323 (2018/04/05)
In this article, we have presented a novel and efficient method for the direct synthesis of unsymmetrical sulfides through the copper(I)-catalyzed cross-coupling of 2-nitro benzenesulfonamides with thiols in the presence of catalytic amount of CuI in DMF as solvent at 100 °C. In addition, the products were obtained in high to excellent yields. More importantly, the novel system showed the primary 2-nitro benzenesulfonamides as a new coupling partner and regioselectively promoted C–S bond-forming transformations through the cleavage of Ar–SO2NH2 bonds.
Fused-Ring Thiadiazines: Preparation and Crystallographic Characterization of 3-Phenyl Derivative of Benzo-, Pyridio[2,3-e]-, Pyrazino[2,3-e]-, and Tetrafluorobenzo-[1,2,4]thiadiazines
Zienkiewicz, Jozef,Kaszynski, Piotr,Young Jr., Victor G.
, p. 2551 - 2561 (2007/10/03)
Four bicyclic 4H-[1,2,4]thiadiazines 1a-d were prepared in 74-88% yields in two steps from the corresponding amidines 2. Three of them, 1a, 1b, and 1d, were obtained by thermal elimination of propene from the intermediate S-propylsulfilimines 12. The pyrazino derivative 1c was formed upon thermolysis of sulfoxide 14c obtained from 2c. The Ei mechanism was investigated using DFT methods. The elimination in the sulfilimine appears to be more favorable by about 2 kcal/mol than in the analogous sulfoxide. Crystal and molecular structures of three out of the four thiadiazines were established by single-crystal X-ray analysis. All thiadiazines were found as the 4H tautomers with the heterocyclic ring puckered along the S(1)...N(4) line. The benzo derivative 1a forms a unidimensional N(4)-H...N(2) chain, the pyrazino derivative 1c forms dimeric pairs with two synergistic hydrogen bonds, and the crystal structure of 1d is characterized by strong C6F 4...C6H5 quadrupolar interactions.
149. Notizen zur Synthese von 2-Aminophenylsulfonen
Courtin, Alfred,Tobel, Hans-Rudolf von,Auerbach, Guenther
, p. 1412 - 1419 (2007/10/02)
Syntheses of the alkyl, cycloalkyl and aryl 2-aminophenyl sulfones 10 were achieved by oxidation of the corresponding 2-nitrophenyl sulfides 7 to the 2-nitrophenyl sulfones 9 followed by ethanolic Bechamp-reduction.The sulfides 7 in turn were obtained by either reactions of 2-nitro-thiophenol (8) with the appropriate alkyl and cycloalkyl halides or of 2-chloro-nitrobenzene (5) with the relevant thiols.Condensation of 2-nitrobenzenesulfinic acid (3) with bromoacetic acid in aqueous alkaline solution led - presumably via 2-nitrophenylsulfonylacetic acid (4) - to methyl2-nitrophenyl sulfone (1), reduction of which gave 2-aminophenyl methyl sulfone (2).Treatment of 2-aminothiophenol (11) with t-butyl alcohol in aqueous sulfuric acid gave 2-aminophenyl t-butyl sulfide (12), which was acetylated to o-t-butylthio-acetanilide (13).Oxidation of the latter to o-t-butylsulfonyl-acetanilide (14) followed by hydrolysis led to 2-aminophenyl t-butyl sulfone (15).
