304460-21-7Relevant articles and documents
Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides
Paz, Nieves R.,Rodríguez-Sosa, Dionisio,Valdés, Haydee,Marticorena, Ricardo,Melián, Daniel,Copano, M. Belén,González, Concepción C.,Herrera, Antonio J.
supporting information, p. 2370 - 2373 (2015/06/02)
Mechanistic evidence observed in Hofmann-L?ffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity. (Chemical Equation Presented).
Flow synthesis and biological activity of aryl sulfonamides as selective carbonic anhydrase IX and XII inhibitors
Rosatelli, Emiliano,Carotti, Andrea,Ceruso, Mariangela,Supuran, Claudiu T.,Gioiello, Antimo
supporting information, p. 3422 - 3425 (2014/07/22)
A series of secondary and tertiary aryl sulfonamides were synthesized under flow conditions and evaluated for their ability to selectively inhibit tumor-associated carbonic anhydrase isoforms IX and XII. The tested compounds revealed to be highly potent CA IX inhibitors in nanomolar range, and to inhibit CA XII activity with different ranks of potencies. Remarkably, 4-methyl-N-phenyl-benzenesulfonamide was a selective nanomolar CA IX inhibitor with an IC50 of 90 nM.
Building a sulfonamide library by eco-friendly flow synthesis
Gioiello, Antimo,Rosatelli, Emiliano,Teofrasti, Michela,Filipponi, Paolo,Pellicciari, Roberto
supporting information, p. 235 - 239 (2013/06/27)
A rapid and eco-friendly synthesis of a sulfonamide library under flow conditions is described. The study illustrates an efficient, safe, and easily scalable preparation of sulfonamides by use of a meso-reactor apparatus, thus demonstrating the impact of flow technologies within drug discovery. Waste minimization, employment of green media, and nontoxic reactants are achieved by the optimization of the flow setup and experimental protocol designed to sequentially synthesize primary, secondary, and tertiary sulfonamides. Isolation of the products involves only extraction and precipitation affording pure compounds in good to high yields without further purification for biological evaluation.
Stereoselective radical Aryl migration reactions from sulfur to carbon
Bossart, Martin,Faessler, Roger,Schoenberger, Jan,Studer, Armido
, p. 2742 - 2757 (2007/10/03)
Stereoselective aryl migration reactions from sulfur in sulfonates and sulfonamides to C-centered radicals are reported. The 1,5-aryl migration from sulfur to differently substituted C-centered radicals could be performed with high yields and selectivities. Functionalized aryl groups could also be transferred by this new method. A model to explain the stereochemical outcome of the reaction is presented and some mechanistic aspects of this reaction are discussed. Aryl migration reactions from sulfur in sulfinates to carbon radicals were less efficient, and the corresponding migrations in aryl sulfoxides were not observed at all. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
SYNTHESIS OF THE RACEMIC FORM OF (Z)-1,17-DIAMINOOCTADEC-9-ENE, AN ALIPHATIC DIAMINE FROM COCCINELLIDAE. DETERMINATION OF THE ABSOLUTE CONFIGURATION OF THE (+)-NATURALLY-OCCURRING ANTIPODE
Braconnier, M.F.,Braekman, J.C.,Daloze, D.
, p. 605 - 614 (2007/10/02)
The total synthesis of the title compound (1) has been achieved.Also reported is the use of lanthanide induced shifts in 1H NMR spectroscopy to assign the absolute configuration of the α-carbon atom in chiral primary α-methylalkylamines.Application of this empirical method to natural (+)-1 shows that it has the R-configuration at C-17.
