Experimental and theoretical investigation of the reaction of 2,5-diphenyl-1,3-oxazole and 2,5-diphenyl-1,3,4-oxadiazole dimethylamino derivatives with the Vilsmeier reagent

• Дата: 2004
• Автори: Semenova, O.N., Galkina, O.S., Patsenker, L.D., Yermolenko, I.G., Fedyunyayeva, I.A.
• Формат: Стаття
• Мова: English
• Опубліковано: НТК «Інститут монокристалів» НАН України 2004
• Назва видання: Functional Materials
• Онлайн доступ: http://dspace.nbuv.gov.ua/handle/123456789/134420
• Назва журналу: Digital Library of Periodicals of National Academy of Sciences of Ukraine
• Цитувати: Experimental and theoretical investigation of the reaction of 2,5-diphenyl-1,3-oxazole and 2,5-diphenyl-1,3,4-oxadiazole dimethylamino derivatives with the Vilsmeier reagent / O.N.Semenova, O.S.Galkina, L.D.Patsenker, I.G.Yermolenko, I.A.Fedyunyayeva // Functional Materials. — 2004. — Т. 11, № 1. — С. 67-75. — Бібліогр.: 21 назв. — англ.

The 2,5-diphenyl-1,3-oxazole and 2,5-diphenyl-1,3,4-oxadiazole dimethylamino deriva¬tives are widely used as organic luminophores. These compounds are found to be substi¬tuted in the ortAo-position to the dimethylamino group under conditions of the Vilsmeier- Haack reaction. The attack by the POCI3-DMF complex results in formation of the "open" iminium salt which is subjected the isomerization into tetrahydroquinazolinium salt. The substitution reaction directed to the 4 position of the oxazole ring causes formylation. The reactivity of the compounds under investigation and the reaction pathways have been studied using the quantum-chemical semi-empirical methods. The most favorable condi - tions for synthesis of the quinazolinium salts and aldehydes have been determined. The compounds obtained are of considerable interest as the water soluble high-efficiency luminophores.