INVESTIGATIONS ON 2,3'-BIQUINOLYL. 16. THE REGIOSELECTIVITY OF REDUCTION OF 1-ALKYL-3-(2-QUINOLYL)QUINOLINIUM AND 1,1'-DIALKYL-3,3'-DI(2-QUINOLYL)-1,1',4,4'-BIQUINOLYL IODIDES USING METALLIC ZINC, LITHIUM AND POTASSIUM

Authors

  • А. В. Аксенов Stavropol State University, Stavropol 355009
  • А. В. Сарапий Stavropol State University, Stavropol 355009
  • О. А. Антонова Stavropol State Medical Academy, Stavropol 355017
  • И. В. Боровлев Stavropol State University, Stavropol 355009
  • В. И. Гончаров Stavropol State Medical Academy, Stavropol 355017

DOI:

https://doi.org/10.1007/8223

Keywords:

1'-alkyl-1', 4'-dihydro-2, 3'-biquinolyls, 1, 1'-dialkyl-3, 3'-di(2-quinolyl)-1, 1', 4, 4'-tetrahydro-4, 4'-biquinolyls, 2'-dihydro-2, 3'-biquinolyl, 1-alkyl-3-(2-quinolyl)quinolinium iodides, potassium, lithium, zinc, reduction

Abstract

The reaction of 1-alkyl-3-(2-quinolyl)quinolinium iodides with excess zinc in THF gives a diastereomeric mixture of 1,1'-dialkyl-3,3'-di(2-quinolyl)-1,1',4,4'-tetrahydro-4,4'-biquinolyls. An excess of lithium in THF gives a mixture of 1',2'-dihydro-2,3'-biquinolyl and 1'-alkyl-1',4'-dihydro-2,3'-biquinolyl with the former predominating. The reduction by lithium in THF of 1,1'-dialkyl-3,3'-di(2-quinolyl)-1,1',4,4'-tetrahydro-4,4'-biquinolyls leads to analogous products. Reduction of 1-alkyl-3-(2-quinolyl)quinolinium iodides by metallic potassium gives 1-alkyl-1',4'-dihydro-2,3'-biquinolyls.

How to Cite
Aksenov, A. V.; Sarapii, A. V.; Antonova, O. A.; Borovlev, I. V.; Goncharov, V. I.  Chem. Heterocycl. Compd. 2005, 41, 1031. [Khim. Geterotsikl. Soedin. 2005, 1208.]

For this article in the English edition, see DOI 10.1007/s10593-005-0274-5


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Published

2023-10-30

Issue

No. 8 (2005)

Section

Original Papers