Study of synthesis of 2-(2-alkoxyphenyl)-1H-imidazoles. Comparison of oxidative aromatization reactions of imidazolines

Autor:	Sylva Senauerova, Karel Handlíř, Vlasta Liskova, Miroslav Ludwig, Patrik Pařík
Rok vydání:	2006
Předmět:	chemistry.chemical_classification organic chemicals Organic Chemistry Aromatization chemistry.chemical_element Halide Alkylation Toluene chemistry.chemical_compound chemistry Organic chemistry heterocyclic compounds Dehydrogenation Isopropyl Alkyl Palladium
Zdroj:	Journal of Heterocyclic Chemistry. 43:835-841
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570430404
Popis:	The reaction of methyl salicylate with ethane-1,2-diamine has been used to prepare 2-(2-hydroxyphenyl)-1H-imidazoline. This compound was alkylated with alkyl halides to give five new 2-(2-alkoxyphenyl)-1H-imidazolines (alkyl = propyl, isopropyl, isobutyl, sec-butyl, benzyl). Seven types of transformation reactions of imidazolines into the respective imidazoles were tested. Out of them successful were the dehydrogenation on palladium in toluene (several-day refluxing), oxidation with activated manganese dioxide in toluene (several-hour heating at 60 °C), and the oxidation with potassium nitrosodisulfonate (Fremy's salt) at room temperature. Seven new 2-(2-alkoxyphenyl)-1H-imidazoles were synthesized (alkyl = ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, benzyl) via mentioned methods. Comparison of individual oxidative aromatization reactions is discussed from the point of view of experimental arrangement, reaction time and conditions, purity of the products obtained, and yields.
Databáze:	OpenAIRE
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