Issue 19, 2021
From the journal:

Organic Chemistry Frontiers

Metal-free regioselective C5-cyanoalkylation of the 8-aminoquinolineamides/sulfonamides via oxidative cross-dehydrogenative coupling with alkylnitriles†

Fatemeh Doraghi, ORCID logo a   Ebrahim Kianmehr ORCID logo *a  and  Alireza Foroumadi*b  

* Corresponding authors

a School of Chemistry, College of Science, University of Tehran, Tehran 1417614411, Iran
E-mail: kianmehr@khayam.ut.ac.ir

b Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
E-mail: aforoumadi@yahoo.com

Abstract

A direct metal-free oxidative cross-dehydrogenative coupling of 8-aminoquinolineamides/sulfonamides and acetonitrile is described. This protocol exhibits good tolerance toward various aryl, heteroaryl and aliphatic carboxamide derivatives. Mechanism investigations reveal that the reaction proceeds via a radical pathway.

Graphical abstract: Metal-free regioselective C5-cyanoalkylation of the 8-aminoquinolineamides/sulfonamides via oxidative cross-dehydrogenative coupling with alkylnitriles

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Article information

DOI
https://doi.org/10.1039/D1QO00570G
Article type
Research Article
Submitted
13 Apr 2021
Accepted
01 Aug 2021
First published
10 Aug 2021

Org. Chem. Front., 2021,8, 5424-5431

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Metal-free regioselective C5-cyanoalkylation of the 8-aminoquinolineamides/sulfonamides via oxidative cross-dehydrogenative coupling with alkylnitriles

F. Doraghi, E. Kianmehr and A. Foroumadi, Org. Chem. Front., 2021, 8, 5424 DOI: 10.1039/D1QO00570G

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