http://hdl.handle.net/20.500.12128/354
Tytuł: | Study of 2-aminoquinolin-4(1H)-one under Mannich and retro-Mannich reaction |
Autor: | Funk, Petr Motyka, Kamil Soural, Miroslav Malon, Michal Koshino, Hiroyuki Kusz, Joachim Hlavac, Jan |
Słowa kluczowe: | Mannich reaction; retro-Mannich reaction; Aminoquinolines |
Data wydania: | 2017 |
Źródło: | PLoS ONE, Vol. 12, iss. 5 (2017), art. no e0175364 |
Abstrakt: | 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. |
URI: | http://hdl.handle.net/20.500.12128/354 |
DOI: | 10.1371/journal.pone.0175364 |
ISSN: | 1932-6203 |
Pojawia się w kolekcji: | Artykuły (WNŚiT) |
Plik | Opis | Rozmiar | Format | |
---|---|---|---|---|
Funk_Study_of_2-aminoquinolin-4(1H)-one_under_Mannich_and_retro_Mannich_reaction.pdf | 1,23 MB | Adobe PDF | Przejrzyj / Otwórz |
Uznanie Autorstwa 3.0 Polska Creative Commons