含窒素複素環化合物の研究(第45報)Isoquinoline類を原料とするCyclopropa[c]isoquinoline誘導体の合成法

概要

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Application of dichlorocarbene to 2-methylisoquinolinium iodides (3), derived from isoquinoline (1), in the presence of a phase-shifting catalyst, resulted in the formation of 1,1-dichloro-2-methyl-3-(trichloromethyl)-1a, 2,3,7b-tetrahydro-1H-cyclopropa [c] isoquinoline derivatives (4). Application of dichlorocarbene to I in the presence of ethanol gave 1,1-dichloro-3-ethoxy-2-formyl-1a, 2,3,7b-tetrahydro-1H-cyclopropa [c] isoquinoline derivative (s) (7). Both 4 and 7 were labile and were obtained in a low yield. Application of dichloro-or dibromo-carbene to 1-alkyl-2-benzoyl-1-cyano-1,2-dihydroisoquinolines (10), obtained from 1 in two steps, afforded stable 2-benzoyl-3-cyano-1,1-dichloro (or -1,1-dibromo)-1a, 2,3,7b-tetrahydro-1H-cyclopropa [c] isoquinoline derivatives (11) in a high yield. Since there has been no published report on the syntheses of cyclopropa [c] isoquinoline derivatives from 1,this method of synthesis via 10 seems to be useful.
公益社団法人日本薬学会の論文
1979-12-25