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.
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).
Domínguez
Laura
L
Laboratorio de Radicales Libres, Instituto de Química Orgánica General, CSIC, C/Juan de la Cierva, 3, 28006-Madrid, Spain.
van Nhien
Albert Nguyen
AN
Tomassi
Cyrille
C
Len
Christophe
C
Postel
Denis
D
Marco-Contelles
José
J
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*
D002254:Carbonates; D009570:Nitriles; D009705:Nucleosides; D013449:Sulfonamides; D013844:Thiazoles; D012266:Ribose; D014994:Xylose