Reactions of quinine with 2-chloro-4,6-dimethoxy-1,3,5-triazine

被引：0

作者：

Sukiennik, Jaroslaw ^{[1
]}

Kasperowicz-Frankowska, Katarzyna ^{[1
]}

Szczesio, Malgorzata ^{[2
]}

Fraczyk, Justyna ^{[1
]}

Kolesinska, Beata ^{[1
]}

Kaminski, Zbigniew J. ^{[1
]}

机构：

[1] Lodz Univ Technol, Inst Organ Chem, Lodz, Poland

[2] Lodz Univ Technol, Inst Gen & Ecol Chem, Lodz, Poland

来源：

ARKIVOC | 2021年

关键词：

Ring opening; quaternization; 4,5-dimethoxy-1,3,5-triazin-2-yl ammonium chloride; aromatic nucleophilic substitution; REAGENTS;

D O I：

10.24820/ark.5550190.p011.363

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：85 / 98

页数：14