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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
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