INVESTIGATIONS OF 2,3′-BIQUINOLYL. 9. REACTION OF 1′,4′-DIHYDRO-2,3′-BIQUINOLYL WITH ORGANOLITHIUM COMPOUNDS

Abstract

The 1′,4′-dihydro-2,3′-biquinolyl reacts with organolithium compounds to form the mixture of 4′-R-1′,4′-dihydro-2,3′-biquinolyls and 2′-R-1′,2′-dihydro-2,3′-biquinolyls in the ratio analogous to the conversion in the series of 2,3′-biquinolyl. The utilization of the complex, the organolithium compound-TMEDA, in this process leads, after treatment of the reaction mixture with water, exclusively to 2′-R-1′,2′-dihydro-2,3′-biquinolyls. Treatment with methyl iodide leads to 1′-methyl-2′-R-1′,2′-dihydro-2,3′-biquinolyls.

Authors: A. V. Aksenov, A. V. Sarapy, Yu. I. Smushkevich.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (8), pp 952-955

http://link.springer.com/article/10.1007/BF02256980