New 4-amino-5- H-2,3-dihydroisothiazole-1,1-dioxides from sugar α-aminonitriles using the CSIC reaction

4-Amino-5- H-2,3-dihydroisothiazole-1,1-dioxide ring was attached to a monosaccharide ring system by carbanion-mediated sulfonate intramolecular cyclisation (CSIC) of either secondary or tertiary aminonitrilesulfonamide carbohydrate derivatives using NaH, Cs 2CO 3 or BuLi as a base. These new bicycl...

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Bibliographic Details
Published in:Tetrahedron letters 2001-01, Vol.42 (4), p.593-595
Main Authors: Postel, Denis, Nguyen Van Nhien, Albert, Villa, Pierre, Ronco, Gino
Format: Article
Language:English
Subjects:
4-amino-5- H-2,3-dihydroisothiazole-1,1-dioxide ring
CSIC reaction
TSAO
α-aminonitriles
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Summary:4-Amino-5- H-2,3-dihydroisothiazole-1,1-dioxide ring was attached to a monosaccharide ring system by carbanion-mediated sulfonate intramolecular cyclisation (CSIC) of either secondary or tertiary aminonitrilesulfonamide carbohydrate derivatives using NaH, Cs 2CO 3 or BuLi as a base. These new bicyclic systems were used as glycone precursors of aza analogues of TSAO RT inhibitors. We report the first synthesis of an aza analogue of TSAO-m 3T. Both secondary and tertiary aminonitrilesulfonamides from sugar lead to 4-amino spiroisothiazole via a CSIC reaction.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)02013-X