Sulfamides (R 1 R 2 N-SO 2 -NR 3 R 4 ) are traditionally prepared by using strong electrophilic and hazardous reagents such as N-sulfamoyl chloride, sulfonyl chloride, phosphorus oxychloride, or phosphorus pentachloride. We report here a safer and more convenient synthetic methodology for large-scale preparation of sulfamides using the N-substituted oxazolidin-2-one derivatives 5 as synthetic equivalent of the corrosive and hazardous N-sulfamoyl chloride. The scope of the use of N-sulfamoyloxazolidinones to prepare nonsymmetrical sulfamides is explored.
Thiadiazole derivatives R 0300The Ring Opening of 3,4-Dichloro-1,2,5-thiadiazole with Metal Amides. A New Synthesis of 3,4-Disubstituted-1,2,5-thiadiazoles. -The ring-opened products (III) can be further treated with various nucleophiles. Reaction of the resulting products with a second nucleophile results in recyclization to 3,4-disubstituted 1,2,5-thiadiazoles. -(MERSCHAERT*, A.; BOQUEL, P.; GORISSEN, H.; VAN HOECK, J.-P.; BORGHESE, A.; ANTOINE, L.; MANCUSO, V.; MOCKEL, A.; VANMARSENILLE, M.; Tetrahedron Lett. 47 (2006) 47, 8285-8288; Lilly Res. Lab., Chem. Proc. R&D, Lilly Dev. Cent. S. A., B-1348 Mont St. Guibert, Belg.; Eng.) -Mais 09-134
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