New n-glucosylated substituted anilines
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POGREBNOI, Vsevolod. New n-glucosylated substituted anilines. In: Chemistry Journal of Moldova, 2015, nr. 2(10), pp. 62-67. ISSN 1857-1727. DOI: https://doi.org/10.19261/cjm.2015.10(2).08
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Chemistry Journal of Moldova
Numărul 2(10) / 2015 / ISSN 1857-1727 /ISSNe 2345-1688

New n-glucosylated substituted anilines
DOI:https://doi.org/10.19261/cjm.2015.10(2).08
CZU: 547.7/.8

Pag. 62-67

Pogrebnoi Vsevolod
 
Institute of Chemistry of the Academy of Sciences of Moldova
 
 
Disponibil în IBN: 28 decembrie 2015


Rezumat

The reaction of ( )-D-glucose 1 with 4-chloroaniline 6b or 3,5-dibromoaniline 12 leads almost exclusively to the β-confi guration of N-glucosylated anilines 7b and 13. Acetylated derivatives 8b, 14 and 15 were obtained by dissolving/suspending substances 7b and 13 in Ac2O/Py mixture. The acetylation of 2-(3,5-dibromophenylamino)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 13 is less selective than in the case of the 2-(4-chlorophenylamino)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 7b and leads to compounds 2-(acetoxymethyl)-6-(3,5-dibromophenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate 14 and 2-(acetoxymethyl)6-(3,5-dibromophenylamino)-5-hydroxytetrahydro-2H-pyran-3,4-diyl diacetate 15 in a 2:1 ratio. The product 14 is formed with greater selectivity and in a higher yield (up to 80%) when the reaction is catalyzed by DMAP and stored for one week at 4oC.

Cuvinte-cheie
N-glucosylated anilines, (+)-D-glucose, 4-chloroaniline, 5-dibromoaniline, Convolutamydines A-E,

3

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<dc:creator>Pogrebnoi, V.S.</dc:creator>
<dc:date>2015-12-14</dc:date>
<dc:description xml:lang='en'>The reaction of ( )-D-glucose 1 with 4-chloroaniline 6b or 3,5-dibromoaniline 12 leads almost exclusively to the β-confi guration of N-glucosylated anilines 7b and 13. Acetylated derivatives 8b, 14 and 15 were obtained by dissolving/suspending substances 7b and 13 in Ac2O/Py mixture. The acetylation of 2-(3,5-dibromophenylamino)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 13 is less selective than in the case of the 2-(4-chlorophenylamino)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 7b and leads to compounds 2-(acetoxymethyl)-6-(3,5-dibromophenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate 14 and 2-(acetoxymethyl)6-(3,5-dibromophenylamino)-5-hydroxytetrahydro-2H-pyran-3,4-diyl diacetate 15 in a 2:1 ratio. The product 14 is formed with greater selectivity and in a higher yield (up to 80%) when the reaction is catalyzed by DMAP and stored for one week at  4oC. </dc:description>
<dc:identifier>10.19261/cjm.2015.10(2).08</dc:identifier>
<dc:source>Chemistry Journal of Moldova 10 (2) 62-67</dc:source>
<dc:subject>N-glucosylated anilines</dc:subject>
<dc:subject>(+)-D-glucose</dc:subject>
<dc:subject>4-chloroaniline</dc:subject>
<dc:subject>3</dc:subject>
<dc:subject>5-dibromoaniline</dc:subject>
<dc:subject>Convolutamydines A-E</dc:subject>
<dc:title>New n-glucosylated substituted anilines</dc:title>
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