INVESTIGATION OF 2,3'-BIQUINOLYL. 10. THE REGIOSELECTIVITY OF THE REACTION OF 2,3'-BIQUINOLYL AND 1'-ALKYL-3-(2-QUINOLYL)QUINOLINIUM HALIDES WITH HALO DERIVATIVES IN THE PRESENCE OF METALLIC LITHIUM AND MAGNESIUM

Abstract

2,3'-Biquinolyl reacts with halo derivatives in the presence of metallic lithium to give addition products at position 4', treatment of which with water gives 4'-R-1',4'-dihydro-2,3'-biquinolyls and with halo derivatives gives 1'-alkyl-4'-R-1',4'-dihydro-2,3'-biquinolyls. The reaction of 2,3'-biquinolyl with halo derivatives in the presence of metallic magnesium gives a mixture of products of addition at positions 2' and 4'. 1-Alkyl-3-(2-quinolyl)quinolinium halides and halo derivatives with metallic magnesium give 1'‑alkyl-2'-R-1',2'-dihydro-2,3'-biquinolyls but form a complex mixture of substances when metallic lithium is used.

Authors: A. V. Aksenov and O. N. Nadein.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (11), pp 1314-1318

http://link.springer.com/article/10.1023/A%3A1017575618900