54129-14-5Relevant academic research and scientific papers
Efficient and Practical Synthesis of Sulfonamides Utilizing SO2 Gas Generated on Demand
Chung Leung, Gulice Yiu,Ramalingam, Balamurugan,Loh, Gabriel,Chen, Anqi
, p. 546 - 554 (2020/04/22)
A simple and practical protocol was developed for the synthesis of sulfonamides by reacting organometallic reagents with SO2 gas generated on demand. SO2 was generated from readily available reagents safely in a highly contained and controlled fashion. The protocol allows the synthesis of sulfonamides without using either atom-inefficient SO2 surrogates or a SO2 cylinder that requires stringent storage regulations in the laboratory. The protocol was successfully applied to the synthesis of sildenafil.
Hypervalent Iodine Mediated Sulfonamide Synthesis
Poeira, Diogo L.,Macara, Jo?o,Faustino, Hélio,Coelho, Jaime A. S.,Gois, Pedro M. P.,Marques, M. Manuel B.
supporting information, p. 2695 - 2701 (2019/04/08)
A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.
Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis
Kim, Taehoon,McCarver, Stefan J.,Lee, Chulbom,MacMillan, David W. C.
supporting information, p. 3488 - 3492 (2018/03/05)
Herein we report a highly efficient method for nickel-catalyzed C?N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N-aryl and N-heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy-transfer mechanism wherein C?N bond reductive elimination occurs from a triplet excited NiII complex. Late-stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated.
ANALYSIS OF SUBSTITUENT AND SOLVENT EFFECTS ON DISSOCIATION OF N-PHENYLBENZENESULPHONAMIDES
Ludwig, Miroslav,Pytela, Oldrich,Javurkova, Helena,Vecera, Miroslav
, p. 2900 - 2908 (2007/10/02)
The potentiometric titration in water, methanol, dimethyl sulphoxide, dimethylformamide, and acetonitrile has been used for determination of pK values of 13 N-arylbenzenesulphonamides.The validity of the Hammett and Yukawa-Tsuno models using several sets of substituent constants has been evaluated by the test to check adequacy of the regression function and by the factor analysis.It has been found that the substituent effects in solvents must be interpreted with regard to the experimental method used, solvent, set of the substituent constants, as well as the model equation ETR.The dependence of the Hammett reaction constants on the solvent has been analyzed and reveals a preferred stabilization of the conjugated base through hydrogen bonds.Direct conjugation of the reaction centre with the substituent and with different extent of the solvent-dependence with the 4-CN and 4-NO2 derivatives have been observed.
