2-O-glycosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F10%3A63509364" target="_blank" >RIV/70883521:28110/10:63509364 - isvavai.cz</a>

Výsledek na webu

—

DOI - Digital Object Identifier

—

Jazyk výsledku

angličtina

Název v původním jazyce

2-O-glycosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones

Popis výsledku v původním jazyce

Some saccharide derivatives of quinolin-2(1H)-one were isolated from natural sources. An example is zeanoside B, which was isolated from corn kernels. Various synthetic compounds of this class possess interesting biological activities; e.g., some 4-glycosyloxy-1-methylquinolin-2(1H)-ones have shown anti-allergic activity. Recently, we identified a method of the selective synthesis of 4-(?-D-glucopyranosyloxy)quinolin-2(1H)-ones by glycosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones. Herein wereport our actual study of glycosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones in other positions. Hydroxyl group of these compounds was protected by acetylation using acetic anhydride in pyridine and the 4-O-acetyl derivatives were treated with 2,3,4,6-tetra-O-acetyl-?-D-glucopyranosyl bromide and silver(I) oxide in acetonitrile. The reaction furnished 2-(2,3,4,6-tetra-O-acetyl-?-D-glucopyrano?syloxy)quinolin-4-yl acetates in satisfactory yields. Structures have been undoubted

Název v anglickém jazyce

2-O-glycosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones

Popis výsledku anglicky

Some saccharide derivatives of quinolin-2(1H)-one were isolated from natural sources. An example is zeanoside B, which was isolated from corn kernels. Various synthetic compounds of this class possess interesting biological activities; e.g., some 4-glycosyloxy-1-methylquinolin-2(1H)-ones have shown anti-allergic activity. Recently, we identified a method of the selective synthesis of 4-(?-D-glucopyranosyloxy)quinolin-2(1H)-ones by glycosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones. Herein wereport our actual study of glycosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones in other positions. Hydroxyl group of these compounds was protected by acetylation using acetic anhydride in pyridine and the 4-O-acetyl derivatives were treated with 2,3,4,6-tetra-O-acetyl-?-D-glucopyranosyl bromide and silver(I) oxide in acetonitrile. The reaction furnished 2-(2,3,4,6-tetra-O-acetyl-?-D-glucopyrano?syloxy)quinolin-4-yl acetates in satisfactory yields. Structures have been undoubted

Druh

D - Stať ve sborníku

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2010

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název statě ve sborníku

Chemické listy

ISBN

—

ISSN

0009-2770

e-ISSN

—

Počet stran výsledku

1

Strana od-do

—

Název nakladatele

Česká společnost chemická

Místo vydání

Praha

Místo konání akce

Nymburk

Datum konání akce

1. 1. 2010

Typ akce podle státní příslušnosti

EUR - Evropská akce

Kód UT WoS článku

—