Introduction of benzo[h]quinoline and 1,10-phenanthroline subunits by Friedlander methodology

被引:165
作者
Riesgo, EC [1 ]
Jin, XQ [1 ]
Thummel, RP [1 ]
机构
[1] UNIV HOUSTON,DEPT CHEM,HOUSTON,TX 77204
关键词
D O I
10.1021/jo952164h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An improved preparation of 8-amino-7-quinolinecarbaldehyde has been developed. The methyl group of 7-methyl-8-nitroquinoline may be oxidized to an aldehyde by treatment first with dimethylformamide dimethyl acetal followed by sodium periodate. Reduction with iron provides the amino aldehyde. An analogous sequence affords 1-amino-2-naphthalenecarbaldehyde. Friedlander condensation of the quinoline derivative with a series of acetylaromatics provides the corresponding 2-aryl-1,10-phenanthrolines. Condensation of either amino aldehyde with 1,3-diacetylbenzene or 2,6-diacetylpyridine provides the expected Friedlander product. Similar chemistry is described for reactions of the amino aldehydes with 1,4-diacetylbenzene, 4,4'-diacetylbiphenyl, 1,5-diacetylanthracene, 1,2,3,4,5,6,7,8-octahydroacridine-1,8-dione, and tetracyclo[6.3.0.0.(4,11)0(5,9)]undecane-2,7-dione (TCU-2,7-dione).
引用
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页码:3017 / 3022
页数:6
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