CINNOLINES .11. QUATERNISATION OF 3- AND 4-PHENYLCINNOLINES AND REDUCTION OF SOME METHYLCINNOLINIUM SALTS

被引:7
作者
AMES, DE
NOVITT, B
WAITE, D
机构
[1] Chemistry Department, Chelsea College of Science and Technology
[2] Department of Organic Chemistry, Aarhus University, Aarhus
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 05期
关键词
D O I
10.1039/j39690000796
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Phenylcinnoline quaternises with methyl iodide to give 1-methyl-3-phenylcinnolinium iodide and a small amount of its 2-methyl isomer, whereas only the 2-methiodide is isolated from quaternisation of 4-phenylcinnoline. 1-Methyl-3-phenylcinnolinium iodide is reduced electrolytically, or with sodium borohydride, to 1,4-dihydro-1-methyl-3- phenylcinnoline and this is reduced polarographically to 2-o-metnylaminophenyl- 1-phenylethylamine, which is also obtained directly from the quaternary salt by reduction with amalgamated zinc and hydrochloric acid. Reduction of 1,3-dimethylcinnolinium iodide by the Clemmensen method, however, gives 1,2-dimethylindole and 1,2-dimethylindoline while 2-methylcinnolinium iodides give the corresponding indole and indoline.
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页码:796 / &
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