Abstract
Features of 5-trichloromethyl-2-aryl-5,6-dihydro-[1,2,4]triazolo[1,5-c]quinazolines formation as result of [5+1]-cyclocondensation of the corresponding [2-(3-aryl-1H-1,2,4-triazole-5-yl)phenyl]amines with chloral hydrate are described in the article. It has been shown that this transformation is regioselective, occurs by refluxing of the initial compounds in acetic acid with formation of 2-aryl-5-trichloromethyl-5,6-dihydro-[1,2,4]triazolo[1,5-c]quinazolines. The possible mechanism of 5,6-dihydro-[1,2,4]triazolo[1,5-c]quinazolines has been proposed and substantiated. It has been shown that the reaction proceeds as step-by-step transformation that includes ANE and AN processes. The 2-phenyl-5-trichloromethyl-5,6-dihydro-[1,2,4]triazolo[1,5-c]quinazoline obtained was studied in reactions with N-nucleophiles. It has been found that regardless of the nature of nucleophile the reaction mentioned above leads to formation of 2-phenyl5-(dichloromethyl)-[1,2,4]triazolo[1,5-c]qinazoline. The mechanism of the transformation mentioned above is given; it is β-elimination on the E1cb-mechanism followed by isomerisation. The structure of the compounds synthesized has been confirmed by the complex of physicochemical methods, including 1H-, 13C-NMR-spectrometry, chromato-massspectrometry, mass-spectrometry and X-ray structural study. A detailed analysis of 1H and 13C-NMR spectral data of the compounds synthesized has been conducted. It has been found that the signals of the carbon atom in position 5 at 79.25-77.95 ppm were characteristic for 2-aryl-5-trichloromethyl-5,6-dihydro-[1,2,4]triazolo[1,5-c]quinazolines, whereas aromatization of the molecule leads to significant deshielding of this carbon atom (163.41 ppm). The prospects of further chemical modification of 2-aryl-5-(dichloromethyl)-[1,2,4]triazolo[1,5-c]quinazolines has been discussed.
Highlights
Features of 5-trichloromethyl-2-aryl-5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazolines formation as result of [5+1]-cyclocondensation of the corresponding [2-(3-aryl-1H-1,2,4-triazole-5-yl)phenyl]amines with chloral hydrate are described in the article
It has been found that regardless of the nature of nucleophile the reaction mentioned above leads to formation of 2-phenyl5-(dichloromethyl)-[1,2,4]triazolo[1,5-c]qinazoline
It has been found that the signals of the carbon atom in position 5 at 79.25-77.95 ppm were characteristic for 2-aryl-5-trichloromethyl-5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazolines, whereas aromatization of the molecule leads to significant deshielding of this carbon atom (163.41 ppm)
Summary
Features of 5-trichloromethyl-2-aryl-5,6-dihydro-[1,2,4]triazolo[1,5-с]quinazolines formation as result of [5+1]-cyclocondensation of the corresponding [2-(3-aryl-1H-1,2,4-triazole-5-yl)phenyl]amines with chloral hydrate are described in the article. Що зазначене перетворення є регіоселективним та легко відбувається при кип’ятінні вихідних сполук у оцтовій кислоті або пропанолі-2 впродовж 6 годин з утворенням 2-арил5-трихлорометил-5,6-дигідро-[1,2,4]триазоло[1,5-с]хіназолінів. Що для 2-арил-5-трихлорометил-5,6-дигідро-[1,2,4]триазоло[1,5-с]хіназолінів характеристичними є сигнали атома карбону положення 5 при 79.25-77.95 м.ч., тоді як ароматизація системи веде до його дезекранування (163.41 м.ч.). Что данное превращение является региоселективным и легко происходит при кипячении исходных соединений в уксусной кислоте или пропаноле-2 с образованием 2-арил-5-трихлорметил-5,6-дигидро-[1,2,4]триазоло[1,5-с]хиназолинов. The aim of the work is to study the features of the reaction between [2-(3-aryl-1H-1,2,4-triazol-5-yl)phenyl]amines with chloralhydrate and transformations of the non-aromatic heterocyclic compounds obtained with the trichlormethyl moiety at sp3-hybridized carbon atom under the action of N-nucleophiles
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