Reactions of isoquinolinium salts with hydroxylamine derivatives, 2nd communication N-(alkyl) and N-(aryl) substituted compounds

被引：3

作者：

Möhrle, H ^{[1
]}

Niessen, R ^{[1
]}

机构：

[1] Univ Dusseldorf, Inst Pharmazeut Chem, D-40225 Dusseldorf, Germany

来源：

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 1999年 / 54卷 / 04期

关键词：

oxime; dioxime; E/Z-enamine; ring-chain isomerism; amine oxide;

D O I：

10.1515/znb-1999-0417

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The N-alkyl- and N-aryl-isoquinolinium salts 7, 15-17 reacted with free hydroxylamine in pyridine to give the isoquinoline-2-oxide (9) as final product. The intermediate dioximes 8 were isolated and characterized by derivatisation with acetic anhydride to the oxime ester nitrile 10. From the reaction of 8 with trifluoroacetic anhydride/triethylamine 3-amino-isoquinoline-2-oxide (12) resulted after hydrolysis. Due to the electronic influence the 5-nitroisoquinolinium salts 1-3 react faster than the 5-hydroxy derivative 20, but with the same course of conversion via dioximes to amine oxides. An optimized method for preparation of the amine oxides was developed.

引用

页码：532 / 540

页数：9

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