ПЕРЕГРУПУВАННЯ ЗАМІЩЕНИХ 1,3-БЕНЗОКСАЗИНІВ В СПОЛУКИ КСАНТЕНОВОГО ТИПУ
The rearrangement patterns of new 1,3-benzoxazines derivatives obtained by condensation of substituted salicylamides with cyclic ketones under the influence of Vilsmeier-Haack reagent has been studied. The influence of angel strain in a 4-membered spirocycle prevents the rearrangement of spiro [1,3-...
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| Дата: | 2020 |
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| Автори: | , , , |
| Формат: | Стаття |
| Мова: | English |
| Опубліковано: |
V.I.Vernadsky Institute of General and Inorganic Chemistry
2020
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| Онлайн доступ: | https://ucj.org.ua/index.php/journal/article/view/124 |
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| Назва журналу: | Ukrainian Chemistry Journal |
Репозитарії
Ukrainian Chemistry Journal| id |
oai:ojs2.1444248.nisspano.web.hosting-test.net:article-124 |
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oai:ojs2.1444248.nisspano.web.hosting-test.net:article-1242020-03-18T17:41:08Z REARRANGEMENT OF SUBSTITUTED 1,3-BENZOXAZINES INTO XANTHENE-TYPE COMPOUNDS ПЕРЕГРУППИРОВКА ЗАМЕЩЁННЫХ 1,3-БЕНЗОКСАЗИНОВ В СОЕДИНЕНИЯ КСАНТЕНОВОГО ТИПА ПЕРЕГРУПУВАННЯ ЗАМІЩЕНИХ 1,3-БЕНЗОКСАЗИНІВ В СПОЛУКИ КСАНТЕНОВОГО ТИПУ Farat, Oleg Varenichenko, Svetlana Zaliznaya, Ekaterina Markov, Victor rearrangement, Vilsmeier–Haack reagent, condensation, 1,3-benzoxazine, xanthene derivatives. The rearrangement patterns of new 1,3-benzoxazines derivatives obtained by condensation of substituted salicylamides with cyclic ketones under the influence of Vilsmeier-Haack reagent has been studied. The influence of angel strain in a 4-membered spirocycle prevents the rearrangement of spiro [1,3-benzoxazine-2,1'-cyclobutan]-4(3H)-one under the action of a formylating agent. 1,3-Benzoxazines derivatives with ring sizes from 5- to 8-membered under the action of a formylating agent have formed formylxanthene derivative. Their formation reaction rate depends on the presence of electronegativity substituents at positions C-6 and C-8 of the aromatic cycle, as well as in the spiroring. In this work, we presented an effective method for the synthesis of formyl derivatives of xanthenes based on readily available salicylamide. It was found that (spiro[1,3-benzoxazine-2,1'-cyclobutan]-4(3H)-one) does not rearrange even under prolonged heating due to the spirocycle strain. The presence of bromine or iodine atoms at positions C-6 and C-8 of the aromatic cycle of 1,3-benzoxazines makes the reaction more difficult, which requires more harsh synthesis conditions. V.I.Vernadsky Institute of General and Inorganic Chemistry 2020-02-05 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/124 10.33609/0041-6045.86.2.2020.111-122 Ukrainian Chemistry Journal; Vol. 86 No. 2 (2020): Ukrainian Chemistry Journal; 111-122 Украинский химический журнал; Том 86 № 2 (2020): Украинский химический журнал; 111-122 Український хімічний журнал; Том 86 № 2 (2020): Український хімічний журнал; 111-122 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/124/79 |
| institution |
Ukrainian Chemistry Journal |
| baseUrl_str |
|
| datestamp_date |
2020-03-18T17:41:08Z |
| collection |
OJS |
| language |
English |
| topic_facet |
rearrangement Vilsmeier–Haack reagent condensation 1,3-benzoxazine xanthene derivatives. |
| format |
Article |
| author |
Farat, Oleg Varenichenko, Svetlana Zaliznaya, Ekaterina Markov, Victor |
| spellingShingle |
Farat, Oleg Varenichenko, Svetlana Zaliznaya, Ekaterina Markov, Victor ПЕРЕГРУПУВАННЯ ЗАМІЩЕНИХ 1,3-БЕНЗОКСАЗИНІВ В СПОЛУКИ КСАНТЕНОВОГО ТИПУ |
| author_facet |
Farat, Oleg Varenichenko, Svetlana Zaliznaya, Ekaterina Markov, Victor |
| author_sort |
Farat, Oleg |
| title |
ПЕРЕГРУПУВАННЯ ЗАМІЩЕНИХ 1,3-БЕНЗОКСАЗИНІВ В СПОЛУКИ КСАНТЕНОВОГО ТИПУ |
| title_short |
ПЕРЕГРУПУВАННЯ ЗАМІЩЕНИХ 1,3-БЕНЗОКСАЗИНІВ В СПОЛУКИ КСАНТЕНОВОГО ТИПУ |
| title_full |
ПЕРЕГРУПУВАННЯ ЗАМІЩЕНИХ 1,3-БЕНЗОКСАЗИНІВ В СПОЛУКИ КСАНТЕНОВОГО ТИПУ |
| title_fullStr |
ПЕРЕГРУПУВАННЯ ЗАМІЩЕНИХ 1,3-БЕНЗОКСАЗИНІВ В СПОЛУКИ КСАНТЕНОВОГО ТИПУ |
| title_full_unstemmed |
ПЕРЕГРУПУВАННЯ ЗАМІЩЕНИХ 1,3-БЕНЗОКСАЗИНІВ В СПОЛУКИ КСАНТЕНОВОГО ТИПУ |
| title_sort |
перегрупування заміщених 1,3-бензоксазинів в сполуки ксантенового типу |
| title_alt |
REARRANGEMENT OF SUBSTITUTED 1,3-BENZOXAZINES INTO XANTHENE-TYPE COMPOUNDS ПЕРЕГРУППИРОВКА ЗАМЕЩЁННЫХ 1,3-БЕНЗОКСАЗИНОВ В СОЕДИНЕНИЯ КСАНТЕНОВОГО ТИПА |
| description |
The rearrangement patterns of new 1,3-benzoxazines derivatives obtained by condensation of substituted salicylamides with cyclic ketones under the influence of Vilsmeier-Haack reagent has been studied. The influence of angel strain in a 4-membered spirocycle prevents the rearrangement of spiro [1,3-benzoxazine-2,1'-cyclobutan]-4(3H)-one under the action of a formylating agent. 1,3-Benzoxazines derivatives with ring sizes from 5- to 8-membered under the action of a formylating agent have formed formylxanthene derivative. Their formation reaction rate depends on the presence of electronegativity substituents at positions C-6 and C-8 of the aromatic cycle, as well as in the spiroring. In this work, we presented an effective method for the synthesis of formyl derivatives of xanthenes based on readily available salicylamide. It was found that (spiro[1,3-benzoxazine-2,1'-cyclobutan]-4(3H)-one) does not rearrange even under prolonged heating due to the spirocycle strain. The presence of bromine or iodine atoms at positions C-6 and C-8 of the aromatic cycle of 1,3-benzoxazines makes the reaction more difficult, which requires more harsh synthesis conditions. |
| publisher |
V.I.Vernadsky Institute of General and Inorganic Chemistry |
| publishDate |
2020 |
| url |
https://ucj.org.ua/index.php/journal/article/view/124 |
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2025-09-24T17:43:23Z |
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2025-09-24T17:43:23Z |
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