title: Synthesis of 4-amino-5-H-2,3-dihydroisothiazole-1,1-dioxide ring systems on sugar templates via carbanion-mediated sulfonamide intramolecular cyclization reactions (CSIC protocols) of glyco-alpha-sulfonamidonitriles.
abstract: The carbanion-mediated sulfonate intramolecular cyclizations (CSIC protocols) of glyco-alpha-sulfonamidonitriles derived from readily available monosaccharides have been extensively investigated using potassium carbonate, cesium carbonate, n-BuLi, and LDA as bases. As a result, a series of enantiomerically pure spiro(4-amino-5-H-2,3-dihydroisothiazole-1,1-dioxide) derivatives have been prepared efficiently and isolated in good yield. The synthesis of these new bicyclic systems is key to accessing a novel range of aza analogues of TSAO nucleosides (ATSAOs).
authors.affiliation: Laboratorio de Radicales Libres, Instituto de Química Orgánica General, CSIC, C/Juan de la Cierva, 3, 28006-Madrid, Spain.
authors.forename: Laura
authors.initials: L
authors.lastname: Domínguez
authors.forename: Albert Nguyen
authors.initials: AN
authors.lastname: van Nhien
authors.forename: Cyrille
authors.initials: C
authors.lastname: Tomassi
authors.forename: Christophe
authors.initials: C
authors.lastname: Len
authors.forename: Denis
authors.initials: D
authors.lastname: Postel
authors.forename: José
authors.initials: J
authors.lastname: Marco-Contelles
mesh_terms: D002254:Carbonates / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009705:Nucleosides / Q000737:chemistry; D012266:Ribose / Q000031:analogs & derivatives*; D013449:Sulfonamides / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014994:Xylose / Q000031:analogs & derivatives*
chemical_list: D002254:Carbonates; D009570:Nitriles; D009705:Nucleosides; D013449:Sulfonamides; D013844:Thiazoles; D012266:Ribose; D014994:Xylose