Conţinutul numărului revistei |
Articolul precedent |
Articolul urmator |
1053 2 |
Ultima descărcare din IBN: 2017-03-17 16:45 |
Căutarea după subiecte similare conform CZU |
547.7/.8 (8) |
Chimie organică (484) |
SM ISO690:2012 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 | ||||||
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DOI:https://doi.org/10.19261/cjm.2015.10(2).08 | ||||||
CZU: 547.7/.8 | ||||||
Pag. 62-67 | ||||||
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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. |
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Cuvinte-cheie N-glucosylated anilines, (+)-D-glucose, 4-chloroaniline, 5-dibromoaniline, Convolutamydines A-E, 3 |
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