4,5-Bis(dimethylamino)quinolines: proton sponge versus azine behavior

Olga V Dyablo; Elena A Shmoilova; Alexander F Pozharskii; Valery A Ozeryanskii; Oleg N Burov; Zoya A Starikova

doi:10.1021/ol301777s

4,5-Bis(dimethylamino)quinolines: proton sponge versus azine behavior

Org Lett. 2012 Aug 17;14(16):4134-7. doi: 10.1021/ol301777s. Epub 2012 Aug 3.

Authors

Olga V Dyablo¹, Elena A Shmoilova, Alexander F Pozharskii, Valery A Ozeryanskii, Oleg N Burov, Zoya A Starikova

Affiliation

¹ Department of Organic Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation.

PMID: 22860688
DOI: 10.1021/ol301777s

Abstract

Two first representatives, 5 and 6, of the still unknown 4,5-bis(dimethylamino)quinoline have been synthesized and studied. While the former, being protonated either at the peri-NMe(2) groups or at the ring nitrogen, has been shown to display properties of both a proton sponge and azine, its counterpart 6 behaves exclusively as azine giving only a quinolinium salt.