197727-60-9Relevant academic research and scientific papers
Metal-Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO2, and Amines
Blum, Stephan P.,Karakaya, Tarik,Schollmeyer, Dieter,Klapars, Artis,Waldvogel, Siegfried R.
supporting information, p. 5056 - 5062 (2021/02/05)
Sulfonamides are among the most important chemical motifs in pharmaceuticals and agrochemicals. However, there is no methodology to directly introduce the sulfonamide group to a non-prefunctionalized aromatic compound. Herein, we present the first dehydrogenative electrochemical sulfonamide synthesis protocol by exploiting the inherent reactivity of (hetero)arenes in a highly convergent reaction with SO2 and amines via amidosulfinate intermediate. The amidosulfinate serves a dual role as reactant and supporting electrolyte. Direct anodic oxidation of the aromatic compound triggers the reaction, followed by nucleophilic attack of the amidosulfinate. Boron-doped diamond (BDD) electrodes and a HFIP–MeCN solvent mixture enable selective formation of the sulfonamides. In total, 36 examples are demonstrated with yields up to 85 %.
Design of Benzoxathiazin-3-one 1,1-Dioxides as a New Class of Irreversible Serine Hydrolase Inhibitors: Discovery of a Uniquely Selective PNPLA4 Inhibitor
Kornahrens, Anne F.,Cognetta, Armand B.,Brody, Daniel M.,Matthews, Megan L.,Cravatt, Benjamin F.,Boger, Dale L.
supporting information, p. 7052 - 7061 (2017/05/31)
The design and examination of 4,1,2-benzoxathiazin-3-one 1,1-dioxides as candidate serine hydrolase inhibitors are disclosed, and represent the synthesis and study of a previously unexplored heterocycle. This new class of activated cyclic carbamates provi
Improved functionalized resin for chemical synthesis
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, (2008/06/13)
A support functionalized by an indole or pyrrole aldehyde is useful for the solid phase synthesis of amide type compounds.
