期刊
ARKIVOC
卷 -, 期 -, 页码 85-98出版社
ARKAT USA INC
DOI: 10.24820/ark.5550190.p011.363
关键词
Ring opening; quaternization; 4,5-dimethoxy-1,3,5-triazin-2-yl ammonium chloride; aromatic nucleophilic substitution
资金
- Lodz University of Technology
Quinine reacts with CDMT in a multistage process, leading to the attachment of two triazinyl substituents to the quinoline molecule, confirmed by various analytical techniques.
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, H-1 and C-13 NMR, and IR spectroscopy.
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