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Reaction of Glycosylisothiocyanates with 2-Chloroethylamine. Synthesis and Structure of N-Nucleoside Analogues
Authors:M Avalos  R Babiano  P Cintas  J Fuentes  J L Jimenez  J C Palacios
Institution:1. Department of Organic Chemistry , University of Extremadura , 06071, Badajoz, (Spain);2. Department of Organic Chemistry , University of Seville , 41071, Seville, (Spain)
Abstract:Abstract

Per-O-acetyl-β- /></span>-glycopyranosylisothiocyanates (<b>3</b> and <b>4</b>) were condensed with 2-chloroethylamine hydrochloride to afford <i>N,N</i>'-bis(per-<i>O</i>-acetyl–β-<span class= /></span>-glycopyranosyl)-<i>N</i>-(2-thiazolin-2-yl)thioureas (<b>5</b> and <b>6</b>) through the glycosylaminoheterocycles (<b>7</b> and <b>8</b>) as intermediates. Compounds <b>7</b> and <b>8</b> were converted into <i>N</i>-(2-thiazolin-2-yl)urea or thioureas (<b>9–11</b>) by reaction with iso(thio)cyanates. Compounds <b>5, 6</b> and <b>9–11</b> show a strong chelated structure due to an intramolecular hydrogen bond, which anchors the <i>E,Z</i> conformation in solution.</td>
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