THE INVESTIGATIONS IN 2,3'-BIQUINOLINE SERIES. 25. SYNTHESIS OF 4-(2-QUINOLINYL)PYRROLO[1,2-<i>a</i>]QUINOLINES AND 4-(2-QUINOLYL)IMIDAZO[1,2-<i>a</i>]QUINOLINES
DOI:
https://doi.org/10.1007/6787Keywords:
2, 3'-biquinoline, 1'-R-3-(2-quinolyl)quinolinium bromides, 7, 14-dibenzoyl-6, 13-di(2-quinolyl)-6a, 13a, 14-tetrahydro-7a, 14a-diazadibenzo[a, h]anthracene, α, β-unsaturated carbonyl compounds, 4-(2-quinolyl)imidazo[1, 2-a]quinolines, 4-(2-quinolinyl)pyrrolo[1, 4-(2-quinolinyl)-1, 3, 3a-tetrahydropyrrolo[1, cyclizationAbstract
A method has been developed for the synthesis of 4-(2-quinolinyl)-1,2,3,3a-tetrahydropyrrolo-[1,2-a]quinolines based on the 1,3-dipolar cycloaddition reaction of α,β-unsaturated carbonyl compounds to 2,3'-biquinolinium salts. Oxidation in benzene using MnO2 gave 4-(2-quinolinyl)pyrrolo[1,2-a]quinolines. It was found that a side product of the 1,3-dipolar cycloaddition is 7,14-di-benzoyl-6,13-di(2-quinolyl)-6a,7,13a,14-tetrahydro-7a,14a-diazadibenzo[a,h]anthracene. Reaction of 1'-phenacyl-2,3'-biquinolinium salts with hydroxylamine in acetic acid gave 4-(2-quinolyl)imidazo-[1,2-a]quinolines.
How to Cite
Glushchenko, T. P.; Aksenov, A. V; Goncharov, V. I. Chem. Heterocycl. Compd. 2009, 45, 351. [Khim. Geterotsikl. Soedin. 2009, 433.]
For this article in the English edition see DOI 10.1007/s10593-009-0267-x
