Synthesis and Reactivities of 1-Methyl-2-trichloromethyl-1,2-dihydroquinolines
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Quaternary quinolinium salts, 1-methyl-, 1,3-dimethyl-, and 1,4-dimethylquinolinium iodide, react with trichloromethyl carbanion, which is generated from chloroform and sodium hydroxide in methanol, to give the 1,2-dihydro adducts, 1-methyl-2-trichloromethyl-1,2-dihydroquinolines. 1,2-Dimethylquinolinium salt gives a different type of addition product and further reaction also occurs with dichlorocarbene to give a dichlorocyclopropane-fused compound under similar reaction conditions. Reduction of the 1,2-dihydro adduct gives 1-methyl-2-trichloromethyl-1,2,3,4-tetrahydroquinoline or 1-methyl-2-dichloromethyldecahydroquinoline depending on the catalyst used. These adducts are useful intermediates for synthesis of chlorine-containing heterocycles.
- 公益社団法人日本薬学会の論文
- 1990-09-25
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