129716-35-4Relevant academic research and scientific papers
Diastereoselective Photoredox-Catalyzed [3 + 2] Cycloadditions of N-Sulfonyl Cyclopropylamines with Electron-Deficient Olefins
White, Dawn H.,Noble, Adam,Booker-Milburn, Kevin I.,Aggarwal, Varinder K.
supporting information, p. 3038 - 3042 (2021/05/04)
A highly diastereoselective, visible-light-induced [3 + 2] cycloaddition between N-sulfonyl cyclopropylamines and electron-deficient olefins is reported. The reactions proceed via the oxidation of a sulfonamide aza-anion by an organic photocatalyst to generate a nitrogen-centered radical. Strain-induced ring opening and intermolecular addition to the olefin generate an intermediate carbon-centered radical that is reduced to an anion prior to 5-exo cyclization. This enables a highly diastereoselective construction of trans-cyclopentanes possessing synthetically useful functional groups.
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.
Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols
Laudadio, Gabriele,Barmpoutsis, Efstathios,Schotten, Christiane,Struik, Lisa,Govaerts, Sebastian,Browne, Duncan L.,No?l, Timothy
supporting information, (2019/04/16)
Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.
Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols
Laudadio, Gabriele,Barmpoutsis, Efstathios,Schotten, Christiane,Struik, Lisa,Govaerts, Sebastian,Browne, Duncan L.,No?l, Timothy
supporting information, p. 5664 - 5668 (2019/04/17)
Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.
PENTAFLUOROPHENYL SULFONAMIDE COMPOUNDS, COMPOSITIONS AND USES THEREOF
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Paragraph 00134; 00136; 00161, (2019/04/16)
The present application relates to sulfonamide containing compounds of Formulae (I) and (II) and compositions containing said compounds effective in the treatment of cell proliferative disorders, in particular cancer, and various methods of use thereof.
PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
Sarkar, Debayan,Ghosh, Manoj Kumar,Rout, Nilendri
supporting information, p. 2360 - 2364 (2018/05/24)
A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.
Mild electrochemical deprotection of N-phenylsulfonyl N-substituted amines derived from (R)-phenylglycinol
Coeffard, Vincent,Thobie-Gautier, Christine,Beaudet, Isabelle,Le Grognec, Erwan,Quintard, Jean-Paul
, p. 383 - 391 (2008/09/18)
The electrochemical reduction of N-phenylsulfonyl N-substituted amines in a protic medium under constant cathodic potential was found to be a mild desulfonylation method, which is able to challenge the chemical ones. The influence of the nature of the N-substituents was considered in order to clarify the mechanistic aspects and to evaluate the scope of the method. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Copper-mediated N-cyclopropylation of azoles, amides, and sulfonamides by cyclopropylboronic acid
Benard, Sebastien,Neuville, Luc,Zhu, Jieping
, p. 6441 - 6444 (2008/12/21)
(Chemical Equation Presented) Reaction of azoles, amides, and sulfonamides in dichloroethane with readily available cyclopropylboronic acid in the presence of copper acetate and sodium carbonate afforded the N-cyclopropyl derivatives in good to excellent
Acetophenone-based linker for solid phase synthesis of secondary amides and sulfonamides on the multipin(TM) support
Bui, Chinh T.,Bray, Andrew M.,Ercole, Francesca,Pham, Yen,Rasoul, Firas A.,Maeji, N. Joe
, p. 3471 - 3474 (2007/10/03)
A new and simple linker has been developed for synthesis of secondary amides and sulfonamides. This application is based on the reductive amination reaction between the acetophenone subunit of the linker and a wide range of primary amines including aliphatic and aromatic amines. Cleavage is effected under mild acidic conditions (20% TFA/DCM) to release the products in good yield and purity.
SYNTHESIS OF METAL FREE PHTHALOCYANINETETRAKIS (N-CYCLOPROPYLSULFONAMIDES)
Yahya, Hazim K.,Dawood, Abed A.
, p. 1541 - 1545 (2007/10/02)
Metal free phthalocyaninetetrakis (N-cyclopropylsulfonamides) have been synthesized and their 1H NMR, IR and thermogravimetric studies were reported.
