1987-58-2Relevant articles and documents
Protonation and anion-binding properties of aromatic sulfonylurea derivatives
Bari?i?, D.,Bregovi?, N.,Cindro, N.,Tomi?i?, V.,Vidovi?, N.
, p. 23992 - 24000 (2021/07/29)
In this work the anion-binding properties of three aromatic sulfonylurea derivatives in acetonitrile and dimethyl sulfoxide were explored by means of NMR titrations. It was found that the studied receptors effectively bind anions of low basicity (Cl?, Br?, I?, NO3?and HSO4?). The stoichiometry of the complexes with receptors containing one binding site was 1?:?1 exclusively, whereas in the case of the receptor containing two sulfonylurea groups 1?:?2 (receptor?:?anion) complexes were also detected in some cases. The presence of strongly basic anions (acetate and dihydrogen phosphate) led to the deprotonation of the sulfonylurea moiety. This completely hindered its anion-binding properties in DMSO and only proton transfer occurred upon the addition of basic anions to the studied receptors. In MeCN, a complex system of equilibria including both ligand deprotonation and anion binding was established. Since ionisation of receptors was proven to be a decisive factor defining the behaviour of the sulfonylurea receptors, their pKavalues were determined using several deprotonation agents in both solvents. The results were interpreted in the context of receptor structures and solvent properties and applied for the identification of the interactions with basic anions.
A facile synthesis of sulfonylureas: Via water assisted preparation of carbamates
Tanwar, Dinesh Kumar,Ratan, Anjali,Gill, Manjinder Singh
, p. 4992 - 4999 (2017/07/11)
A novel and simple approach to the synthesis of sulfonylureas has been reported. It involved the reaction of various amines with diphenyl carbonate to yield the corresponding carbamates, which subsequently reacted with different sulphonamides to produce different sulfonylureas in excellent yields. The first reaction of diphenyl carbonate with amines was carried out in aqueous:organic (H2O:THF, 90:10) medium at room temperature to produce carbamates that paved a straightforward route to sulfonylureas after reaction with sulfonamides. The above process avoided traditional multistep protocols and the use of hazardous, irritant, toxic and moisture sensitive reagents such as phosgene, isocyanates and/or chloroformates.
Product-Derived Bimetallic Palladium Complex Catalyzes Direct Carbonylation of Sulfonylazides
Zhao, Jin,Li, Zongyang,Song, Shaole,Wang, Ming-An,Fu, Bin,Zhang, Zhenhua
supporting information, p. 5545 - 5549 (2016/05/09)
A novel product-derived bimetallic palladium complex catalyzes a sulfonylazide-transfer reaction with the σ-donor/π-acceptor ligand CO, and is advantageous given its broad substrate scope, high efficiency, and mild reaction conditions (atmospheric pressure of CO at room temperature). This methodology provides a new approach to sulfonylureas, which are present in both pharmaceuticals and agrochemicals. The synthesis of Glibenclamide on a gram scale further revealed the practical utility of this procedure. Mechanistically, the generation of a bridged bimetallic palladium species derived from the product sulfonylurea is disclosed as the crucial step for this catalytic cycle.
