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

Authors
Postel, D Van Nhien, AN Villa, P Ronco, G
Citation
D. Postel et al., New 4-amino-5-H-2, 3-dihydroisothiazole-1,1-dioxides from sugar alpha-aminonitriles using the CSIC reaction, TETRAHEDR L, 42(4), 2001, pp. 593-595
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
4
Year of publication
2001
Pages
593 - 595
Database
ISI
SICI code
0040-4039(20010122)42:4<593:N43FSA>2.0.ZU;2-6
Abstract
4-Amino-5-H-2,3-dihydroisothiazole-1,1-dioxide ring was attached to a monos accharide ring system by carbanion-mediated sulfonate intramolecular cyclis ation (CSIC) of either secondary or tertiary aminonitrilesulfonamide carboh ydrate derivatives using NaH, Cs2CO3, or BuLi as a base. These new bicyclic systems were used as glycone precursors of aza analogues of TSAO RT inhibi tors. We report the first synthesis of an aza analogue of TSAO-m(3)T. (C) 2 001 Elsevier Science Ltd. All rights reserved.