Author:
Böhm Stanislav,Kubík Richard,Hradilek Martin,Němeček Jan,Hušák Michal,Pakhomova Svetlana,Ondráček Jan,Kratochvíl Bohumil,Kuthan Josef
Abstract
2-Phenyl-3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridine (I) was converted to corresponding 1-alkyl-2-phenyl-3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridinium salts III - VI and 2-phenyl- 3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridinium perchlorate (VII). The protonation site is discussed in terms of calculated molecular energies of alternative cations. The X-ray structure analyses of enone I and its quaternary periodide III are reported and compared with the PM3 molecular optimizations. 1H NMR and 13C NMR spectra reveal well changes of molecular structures caused by the transformation of the base I into salts III - VII.
Publisher
Institute of Organic Chemistry & Biochemistry
Cited by
6 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献
1. ChemInform Abstract: Sterically Crowded Heterocycles. Part 1. Molecular Structure of 3- Chain Substituted 2-Phenylimidazo(1,2-a)pyridinium Salts;ChemInform;2010-08-17
2. Sterically Crowded Heterocycles. XIII. An Insight Into the Absolute Stereochemistry of Atropisomeric (Z)-3-(Imidazo[1,2-a]pyridin-3-yl)prop-2-en-1-ones;Collection of Czechoslovak Chemical Communications;2000
3. 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;Collection of Czechoslovak Chemical Communications;1997
4. Sterically Crowded Heterocycles. IV. Diastereoisomeric Products by Ferricyanide Oxidation of Quaternary Pyridinium Salts;Collection of Czechoslovak Chemical Communications;1996
5. Photoisomerization of imidazo[l,2-a]pyridines;Mendeleev Communications;1996