Quinoline誘導体を原料とするCyclopropa[c]quinoline誘導体の1Step合成法

概要

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Reaction of commercial quinoline derivatives (1a-r), dissolved in chloroform and added with ethanol and sodium hydroxide solution, in the presence of triethylbenzylammonium hydroxide, at room temperature resulted in the formation of 1,1-dichloro-2-ethoxy-3-formyl-1a, 2,3,7b-tetrahydro-1H-cyclopropa [c] quinoline derivatives (2a-h) in one step, in a good yield. The use of methanol in place of ethanol gave 1,1-dichloro-3-formyl-2-methoxy-1a, 2,3-7b-tetrahydro-1H-cyclopropa [c] quinoline (9a). Examination of the effect of substituents in 1a to 1r on the formation of cyclopropa [c] quinoline derivatives by this reaction showed that the reaction with dichlorocarbene did not proceed as expected when there was an electron-attracting group like NO_2 in the benzene ring of 1a to 1r, while the compounds like 2a to 2h were formed when there was an electron-donating group like CH_3 and CH_3O was present. Application of methylmagnesium iodide to 2a in ether produced 1,1-dichloro-2-methyl-1a, 2,3,7b-tetrahydro-1H-cyclopropa [c] quinoline (3).
公益社団法人日本薬学会の論文
1979-08-25