Unknown

Dataset Information

0

Study of 2-aminoquinolin-4(1H)-one under Mannich and retro-Mannich reaction.


ABSTRACT: 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.

SUBMITTER: Funk P 

PROVIDER: S-EPMC5448738 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

altmetric image

Publications

Study of 2-aminoquinolin-4(1H)-one under Mannich and retro-Mannich reaction.

Funk Petr P   Motyka Kamil K   Soural Miroslav M   Malon Michal M   Koshino Hiroyuki H   Kusz Joachim J   Hlavac Jan J  

PloS one 20170530 5


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  ...[more]

Similar Datasets

| S-EPMC6026460 | biostudies-literature
| S-EPMC4059224 | biostudies-literature
| S-EPMC4281096 | biostudies-literature
| S-EPMC7880990 | biostudies-literature
| S-EPMC5424441 | biostudies-literature
| S-EPMC2610808 | biostudies-literature
| S-EPMC8270933 | biostudies-literature
| S-EPMC4734417 | biostudies-literature
| S-EPMC3478581 | biostudies-literature
| S-EPMC7756638 | biostudies-literature