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
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-...
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| Дата: | 2004 |
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| Автори: | , , , , |
| Формат: | Стаття |
| Мова: | English |
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НТК «Інститут монокристалів» НАН України
2004
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| Назва видання: | Functional Materials |
| Онлайн доступ: | http://dspace.nbuv.gov.ua/handle/123456789/134420 |
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| 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. |
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irk-123456789-1344202018-06-14T14:22:31Z 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 Semenova, O.N. Galkina, O.S. Patsenker, L.D. Yermolenko, I.G. Fedyunyayeva, I.A. 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. Диметиламинозамещенные 2,5-диарил-1,3,4-оксадиазолы и 2,5-диарил-1,3-оксазолы широко применяются в качестве органических люминофоров. Установлено, что в усло¬виях реакции Bильсмaйера-Xаака эти соединения замещаются в орто-положении к диметиламиногруппе. Атака комплексом POCI3-DMF приводит к образованию "откры¬той" иминиевой соли, которая затем изомеризуется в тетрагидрохиназолиниевую соль. Реакция замещения, направленная в положение 4 оксазольного цикла, приводит к формилированию. Реакционная способность исследуемых соединений и механизмы ре¬акций исследованы с применением квантово-химических полуэмпирических методов. Определены оптимальные условия синтеза хиназолиниевых солей и альдегидов. Полу¬ченные соединения представляют значительный интерес как водорастворимые люмино¬форы высокой эффективности. 2004 Article 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. 1027-5495 http://dspace.nbuv.gov.ua/handle/123456789/134420 en Functional Materials НТК «Інститут монокристалів» НАН України |
| institution |
Digital Library of Periodicals of National Academy of Sciences of Ukraine |
| collection |
DSpace DC |
| language |
English |
| description |
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. |
| format |
Article |
| author |
Semenova, O.N. Galkina, O.S. Patsenker, L.D. Yermolenko, I.G. Fedyunyayeva, I.A. |
| spellingShingle |
Semenova, O.N. Galkina, O.S. Patsenker, L.D. Yermolenko, I.G. Fedyunyayeva, I.A. 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 Functional Materials |
| author_facet |
Semenova, O.N. Galkina, O.S. Patsenker, L.D. Yermolenko, I.G. Fedyunyayeva, I.A. |
| author_sort |
Semenova, O.N. |
| title |
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 |
| title_short |
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 |
| title_full |
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 |
| title_fullStr |
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 |
| title_full_unstemmed |
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 |
| title_sort |
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 |
| publisher |
НТК «Інститут монокристалів» НАН України |
| publishDate |
2004 |
| url |
http://dspace.nbuv.gov.ua/handle/123456789/134420 |
| citation_txt |
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. |
| series |
Functional Materials |
| work_keys_str_mv |
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| first_indexed |
2023-10-18T21:07:45Z |
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2023-10-18T21:07:45Z |
| _version_ |
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