Study of 2-aminoquinolin-4(1H)-one under Mannich and Retro-Mannich Reaction

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F17%3A73583745" target="_blank" >RIV/61989592:15110/17:73583745 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61989592:15310/17:73583745

Výsledek na webu

<a href="http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0175364" target="_blank" >http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0175364</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1371/journal.pone.0175364" target="_blank" >10.1371/journal.pone.0175364</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Study of 2-aminoquinolin-4(1H)-one under Mannich and Retro-Mannich Reaction

Popis výsledku v původním jazyce

2-Aminoquinolin-4(1H)-one was reacted with various primary/secondary amines and paraformaldehyde under Mannich reaction conditions. In the case of secondary amines, the reaction in N,N-dimethylformamide yielded expected Mannich products accompanied with 3,3′-methylenebis(2-aminoquinolin-4(1H)-one). Except these main products, the pyrimido [4,5-b]quinolin-5-one derivative was also identified as co-product. The reaction with primary amines led to the formation of pyrimido[4,5-b]quinolin-5-ones. The Mannich reaction products were thermally unstable and afforded a mixture of bis-(2-aminoquinolin-4(1H)-one) and tris-(2-aminoquinolin-4(1H)-one) derivative, probably via reactive methylene species. This retro-Mannich reaction was tested in reaction with indole and thiophenole as nucleophilles, and appropriate conjugates were formed. The mechanism of above discussed reactions in which 2-aminoquinolinone displays the nucleophilicity on C3 carbon as well as N2 nitrogen is discussed.

Název v anglickém jazyce

Study of 2-aminoquinolin-4(1H)-one under Mannich and Retro-Mannich Reaction

Popis výsledku anglicky

2-Aminoquinolin-4(1H)-one was reacted with various primary/secondary amines and paraformaldehyde under Mannich reaction conditions. In the case of secondary amines, the reaction in N,N-dimethylformamide yielded expected Mannich products accompanied with 3,3′-methylenebis(2-aminoquinolin-4(1H)-one). Except these main products, the pyrimido [4,5-b]quinolin-5-one derivative was also identified as co-product. The reaction with primary amines led to the formation of pyrimido[4,5-b]quinolin-5-ones. The Mannich reaction products were thermally unstable and afforded a mixture of bis-(2-aminoquinolin-4(1H)-one) and tris-(2-aminoquinolin-4(1H)-one) derivative, probably via reactive methylene species. This retro-Mannich reaction was tested in reaction with indole and thiophenole as nucleophilles, and appropriate conjugates were formed. The mechanism of above discussed reactions in which 2-aminoquinolinone displays the nucleophilicity on C3 carbon as well as N2 nitrogen is discussed.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/LO1304" target="_blank" >LO1304: Podpora udržitelnosti Ústavu molekulární a translační medicíny</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

PLoS One

ISSN

1932-6203

e-ISSN

—

Svazek periodika

12

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

15

Strana od-do

"e0175364"

Kód UT WoS článku

000402607000003

EID výsledku v databázi Scopus

—