Collect. Czech. Chem. Commun. 1997, 62, 1599-1611
https://doi.org/10.1135/cccc19971599

Sterically Crowded Heterocycles. IX. New α,β-Unsaturated Ketones Containing Imidazo[1,2-a]quinoline, Imidazo[2,1-a]isoquinoline, Benzo[h]imidazo[1,2-a]quinoline and Imidazo[1,2-a]-1,10-phenanthroline Moieties

Stanislav Böhm, Tomáš Strnad, Iveta Ruppertová and Josef Kuthan

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic

This article is part of serial Sterically crowded heterocycles.

Abstract

(Z)-1,3-Diphenyl-3-(2-phenylimidazo[1,2-a]heteroaryl)prop-2-en-1-ones 2-6 and isomeric [1-heteroaryl-3,5-diphenylpyrrol-2-yl]phenylmethanones 17-20 were prepared by the ferricyanide oxidation of quaternary pyridinium salts 12-16. Axial chirality and helicity of the molecules of 4 and 6 are discussed using various energy data obtained by the quantum chemical PM3 method.

Keywords: Imidazo[1,2-a]quinolines; Imidazo[2,1-a]isoquinolines; Benzo[h]imidazo[1,2-a]quinolines; Imidazo[1,2-a]-1,10-phenanthrolines; Ferricyanide oxidation; Pyridinium salts; Axial chirality; Helicity.