Stereochemistry of the reduction of α-chloroketones with sodium borohydride-application to 3-chloroquinoline-2,4-diones: Dedicated to the memory of Professor Dr. Vojeslav Štěrba who died in September 2015 being nearly 93 years old

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F16%3A43874516" target="_blank" >RIV/70883521:28110/16:43874516 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.tet.2016.05.087" target="_blank" >http://dx.doi.org/10.1016/j.tet.2016.05.087</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tet.2016.05.087" target="_blank" >10.1016/j.tet.2016.05.087</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Stereochemistry of the reduction of α-chloroketones with sodium borohydride-application to 3-chloroquinoline-2,4-diones: Dedicated to the memory of Professor Dr. Vojeslav Štěrba who died in September 2015 being nearly 93 years old

Popis výsledku v původním jazyce

3-Chloroquinoline-2,4-diones were reduced with sodium borohydride to give syn- and anti-chlorohydrins, the stereochemistry of which was established by NMR spectroscopy. Both stereoisomeric chlorohydrins were reacted with potassium carbonate in methanol. anti-Isomers afforded the corresponding epoxides or rearranged to 3-hydroxy-4-alkylquinolin-2-ones, whereas syn-isomers did not react. However, these isomers converted to 4-hydroxyquinolin-2-ones after standing for a long period of time in DMSO. After reaction with thionyl chloride, the syn-isomers yielded cis- and trans-3,4-dichloroquinolin-2-ones.

Název v anglickém jazyce

Stereochemistry of the reduction of α-chloroketones with sodium borohydride-application to 3-chloroquinoline-2,4-diones: Dedicated to the memory of Professor Dr. Vojeslav Štěrba who died in September 2015 being nearly 93 years old

Popis výsledku anglicky

3-Chloroquinoline-2,4-diones were reduced with sodium borohydride to give syn- and anti-chlorohydrins, the stereochemistry of which was established by NMR spectroscopy. Both stereoisomeric chlorohydrins were reacted with potassium carbonate in methanol. anti-Isomers afforded the corresponding epoxides or rearranged to 3-hydroxy-4-alkylquinolin-2-ones, whereas syn-isomers did not react. However, these isomers converted to 4-hydroxyquinolin-2-ones after standing for a long period of time in DMSO. After reaction with thionyl chloride, the syn-isomers yielded cis- and trans-3,4-dichloroquinolin-2-ones.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2016

Kód důvěrnosti údajů

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

Název periodika

Tetrahedron

ISSN

0040-4020

e-ISSN

—

Svazek periodika

72

Číslo periodika v rámci svazku

30

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

8

Strana od-do

4490-4497

Kód UT WoS článku

000380073300002

EID výsledku v databázi Scopus

2-s2.0-84976530940