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

Result code in 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>

Alternative codes found

RIV/61989592:15310/17:73583745

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

<a href="/en/project/LO1304" target="_blank" >LO1304: Support of suistainability of the Institute of Molecular and Translational Medicine</a><br>

Continuities

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

Publication year

2017

Confidentiality

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

Name of the periodical

PLoS One

ISSN

1932-6203

e-ISSN

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Volume of the periodical

12

Issue of the periodical within the volume

5

Country of publishing house

US - UNITED STATES

Number of pages

15

Pages from-to

"e0175364"

UT code for WoS article

000402607000003

EID of the result in the Scopus database

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