J. Sukiennik, Katarzyna Kasperowicz-Frankowska, M. Szczesio
Nov 18, 2020
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Arkivoc
Abstract
Quinine reacts with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) via a multistage process leading to destruction of the quinuclidine fragment and attachment of two triazinyl substituents. In the first, reversible stage, CDMT reacts with the aromatic nitrogen of the quinoline, followed by the slow migration of triazine moiety on the bridgehead nitrogen atom of quinuclidine. The bicyclic system, after quaternization with CDMT, was opened by privileged attack of nucleophilic chloride on methylene carbon in the bridge substituted with vinyl group. In the final stage the second 4,6-dimethoxy-1,3,5-triazin-2-yl moiety was attached to the hydroxy group. The product structure was confirmed by X-ray crystallographic measurements, MS, 1H and 13C NMR, and IR spectroscopy.