Reaction of 3-chloroquinoline-2,4-diones with ethanolamine and rearrangement of the reaction products

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F17%3A63516809" target="_blank" >RIV/70883521:28110/17:63516809 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/62690094:18470/17:50005557

Výsledek na webu

<a href="http://www.sciencedirect.com/science/article/pii/S0040402017301308?via%3Dihub" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0040402017301308?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tet.2017.02.007" target="_blank" >10.1016/j.tet.2017.02.007</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Reaction of 3-chloroquinoline-2,4-diones with ethanolamine and rearrangement of the reaction products

Popis výsledku v původním jazyce

The reaction of tertiary α-chloroketones with ethanolamine has not been hitherto described in the literature. Herein, we describe the reaction of tertiary 3-chloroquinoline-2,4-diones with ethanolamine to give novel 3-(2-hydroxyethylamino)quinoline-2,4-diones. These compounds provide 3-(2-oxooxazolidin-3-yl)quinoline-2,4(1H,3H)-diones and new compounds with dimeric character after reaction with triphosgene. Molecular rearrangement proceeds during the reaction of 3-(2-hydroxyethylamino)quinoline-2,4-diones with isocyanic acid. Three types of reaction products arise: 2-(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-diones, 3-(2-hydroxyethyl)-3,3a-dihydro-2H-imidazo[4,5-]quinoline-4(5H)diones and primarily 5-hydroxy-1-(hydroxyethyl)-1′H-spiro[imidazolidine-5,3′-indole]-2,2′-diones. The reaction mechanism and product stereochemistry are discussed. The 1H, 13C and 15N NMR spectra of the prepared compounds were measured, and all resonances were assigned from appropriate two-dimensional experiments.

Název v anglickém jazyce

Reaction of 3-chloroquinoline-2,4-diones with ethanolamine and rearrangement of the reaction products

Popis výsledku anglicky

The reaction of tertiary α-chloroketones with ethanolamine has not been hitherto described in the literature. Herein, we describe the reaction of tertiary 3-chloroquinoline-2,4-diones with ethanolamine to give novel 3-(2-hydroxyethylamino)quinoline-2,4-diones. These compounds provide 3-(2-oxooxazolidin-3-yl)quinoline-2,4(1H,3H)-diones and new compounds with dimeric character after reaction with triphosgene. Molecular rearrangement proceeds during the reaction of 3-(2-hydroxyethylamino)quinoline-2,4-diones with isocyanic acid. Three types of reaction products arise: 2-(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-diones, 3-(2-hydroxyethyl)-3,3a-dihydro-2H-imidazo[4,5-]quinoline-4(5H)diones and primarily 5-hydroxy-1-(hydroxyethyl)-1′H-spiro[imidazolidine-5,3′-indole]-2,2′-diones. The reaction mechanism and product stereochemistry are discussed. The 1H, 13C and 15N NMR spectra of the prepared compounds were measured, and all resonances were assigned from appropriate two-dimensional experiments.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2017

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

73

Číslo periodika v rámci svazku

12

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

11

Strana od-do

1583-1593

Kód UT WoS článku

000395611800008

EID výsledku v databázi Scopus

2-s2.0-85011990222