Alexander Nikolaevich Larin, Elena Kimovna Avakyan, Oleg Demidov, Anastasia Alekseevna Borovleva, Alexander A. Zubenko, Diana Yu. Pobedinskaya, Artem Pavlovich Ermolenko, Stepan E. Kolosov, Ivan V. Borovlev
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An Oxidative SNH Alkylamination of 5(6,7,8)-Nitroquinoline N-Oxides in Aqueous Dioxane Medium
A novel and efficient method for the synthesis of 2-alkylamino and 2-dialkylamino derivatives of N-oxides of 5-, 6-, 7- and 8-nitroquinolines, which can potentially exhibit biological activity, as containing a pharmacophoric quinoline fragment, is described herein. The reactions of 5(6,7,8)-nitroquinoline N-oxides with various primary or secondary amines in the presence of potassium ferricyanide at in aqueous dioxane medium afforded the corresponding secondary and tertiary amines in moderate to excellent yields. This reaction is the first example of a Chichibabin reaction leading to the formation of 2-alkylaminoquinoline derivatives at position 2 under mild conditions. A study of the antibacterial activity of some products was carried out.
期刊介绍:
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.