ARYLTELLUROCHLORINATION OF 5-ARYL(HETERYL)SUBSTITUTED N-ALLYL-1,2,4-TRIAZOLE-3-THIONE DERIVATIVES
Condensed heterocycles based on 1,2,4-triazole have a wide range of biological activity. The introduction of a pharmacophore fragment of an aryl tertiary residue into their composition can significantly increase the bioactivity of the obtained compounds. Therefore, the synthesis of condensed derivat...
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V.I.Vernadsky Institute of General and Inorganic Chemistry
2023
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oai:ojs2.1444248.nisspano.web.hosting-test.net:article-5782024-02-05T19:10:16Z ARYLTELLUROCHLORINATION OF 5-ARYL(HETERYL)SUBSTITUTED N-ALLYL-1,2,4-TRIAZOLE-3-THIONE DERIVATIVES Onisko, Mikhailo Kut , Mykola Sukharev, Serhii Lendel , Vasyl electrophilic intramolecular cyclisation, annulation, organotellurium compounds, thiazolo[2,3-c][1,2,4]triazole, salt. Condensed heterocycles based on 1,2,4-triazole have a wide range of biological activity. The introduction of a pharmacophore fragment of an aryl tertiary residue into their composition can significantly increase the bioactivity of the obtained compounds. Therefore, the synthesis of condensed derivatives of symmetrical 1,2,4-triazole with aryltellurium fragment is an urgent task. One of the most convenient and effective methods for introducing an aryltellurium fragment into such systems is the method of electrophilic intramolecular cyclisation of alkenyl derivatives of azaheterocycles. The aim of this work was to determine the effect of the nature of the substituent at position five of the initial N-allyl derivatives of 1,2,4-triazol-3-thione on the regioselectivity of electrophilic heterocyclization with p-methoxyphenyltellurium trichloride. The reaction of tellurium-induced heterocyclisation of N-allyl-substituted 1,2,4-triazole-3-thione with was carried out in acetic acid medium at room temperature under stirring for 12 hours. It was found that the reactions of 5-aryl(heteryl)substituted N-allyl derivatives of 1,2,4-triazole-3-thione with p-methoxyphenyltellurium trichloride lead to the formation of chlorides 6-((dichloro(4-methoxyphenyl)-λ4-tellanyl)methyl)-5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-1-ium chlorides with an exocyclic p-methoxyphenyltellurium fragment. The yield of the obtained thiazolotriazolium salts was 68-87%. It should be noted that the use of a double amount of electrophilic reagent did not lead to the formation of a thiazolotriazole complex with p-methoxyphenyltellurium trichloride, which was observed during the heterocyclisation of S-alkenyl derivatives of 1,2,4-triazole. Thus, the tellurium-induced cyclization of 5-substituted N-allyl derivatives of 1,2, 4-triazol-3-thione derivatives by p-methoxyphenyltellurium trichloride is regioselective with the formation of 6-((dichloro(4-methoxyphenyl)-λ4-tellanyl)methyl)-5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-1-ium chlorides and annulation of the thiazoline cycle. The introduction of aryl and heteryl substituents of different nature does not affect the regioselectivity of the heteroannulation process. V.I.Vernadsky Institute of General and Inorganic Chemistry 2023-09-29 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/578 10.33609/2708-129X.89.08.2023.109-116 Ukrainian Chemistry Journal; Vol. 89 No. 8 (2023): Ukrainian Chemistry Journal; 109-116 Украинский химический журнал; Том 89 № 8 (2023): Ukrainian Chemistry Journal; 109-116 Український хімічний журнал; Том 89 № 8 (2023): Ukrainian Chemistry Journal; 109-116 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/578/295 |
| institution |
Ukrainian Chemistry Journal |
| baseUrl_str |
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| datestamp_date |
2024-02-05T19:10:16Z |
| collection |
OJS |
| language |
English |
| topic_facet |
electrophilic intramolecular cyclisation annulation organotellurium compounds thiazolo[2,3-c][1,2,4]triazole salt. |
| format |
Article |
| author |
Onisko, Mikhailo Kut , Mykola Sukharev, Serhii Lendel , Vasyl |
| spellingShingle |
Onisko, Mikhailo Kut , Mykola Sukharev, Serhii Lendel , Vasyl ARYLTELLUROCHLORINATION OF 5-ARYL(HETERYL)SUBSTITUTED N-ALLYL-1,2,4-TRIAZOLE-3-THIONE DERIVATIVES |
| author_facet |
Onisko, Mikhailo Kut , Mykola Sukharev, Serhii Lendel , Vasyl |
| author_sort |
Onisko, Mikhailo |
| title |
ARYLTELLUROCHLORINATION OF 5-ARYL(HETERYL)SUBSTITUTED N-ALLYL-1,2,4-TRIAZOLE-3-THIONE DERIVATIVES |
| title_short |
ARYLTELLUROCHLORINATION OF 5-ARYL(HETERYL)SUBSTITUTED N-ALLYL-1,2,4-TRIAZOLE-3-THIONE DERIVATIVES |
| title_full |
ARYLTELLUROCHLORINATION OF 5-ARYL(HETERYL)SUBSTITUTED N-ALLYL-1,2,4-TRIAZOLE-3-THIONE DERIVATIVES |
| title_fullStr |
ARYLTELLUROCHLORINATION OF 5-ARYL(HETERYL)SUBSTITUTED N-ALLYL-1,2,4-TRIAZOLE-3-THIONE DERIVATIVES |
| title_full_unstemmed |
ARYLTELLUROCHLORINATION OF 5-ARYL(HETERYL)SUBSTITUTED N-ALLYL-1,2,4-TRIAZOLE-3-THIONE DERIVATIVES |
| title_sort |
aryltellurochlorination of 5-aryl(heteryl)substituted n-allyl-1,2,4-triazole-3-thione derivatives |
| description |
Condensed heterocycles based on 1,2,4-triazole have a wide range of biological activity. The introduction of a pharmacophore fragment of an aryl tertiary residue into their composition can significantly increase the bioactivity of the obtained compounds. Therefore, the synthesis of condensed derivatives of symmetrical 1,2,4-triazole with aryltellurium fragment is an urgent task. One of the most convenient and effective methods for introducing an aryltellurium fragment into such systems is the method of electrophilic intramolecular cyclisation of alkenyl derivatives of azaheterocycles. The aim of this work was to determine the effect of the nature of the substituent at position five of the initial N-allyl derivatives of 1,2,4-triazol-3-thione on the regioselectivity of electrophilic heterocyclization with p-methoxyphenyltellurium trichloride.
The reaction of tellurium-induced heterocyclisation of N-allyl-substituted 1,2,4-triazole-3-thione with was carried out in acetic acid medium at room temperature under stirring for 12 hours. It was found that the reactions of 5-aryl(heteryl)substituted N-allyl derivatives of 1,2,4-triazole-3-thione with p-methoxyphenyltellurium trichloride lead to the formation of chlorides 6-((dichloro(4-methoxyphenyl)-λ4-tellanyl)methyl)-5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-1-ium chlorides with an exocyclic p-methoxyphenyltellurium fragment. The yield of the obtained thiazolotriazolium salts was 68-87%. It should be noted that the use of a double amount of electrophilic reagent did not lead to the formation of a thiazolotriazole complex with p-methoxyphenyltellurium trichloride, which was observed during the heterocyclisation of S-alkenyl derivatives of 1,2,4-triazole.
Thus, the tellurium-induced cyclization of 5-substituted N-allyl derivatives of 1,2, 4-triazol-3-thione derivatives by p-methoxyphenyltellurium trichloride is regioselective with the formation of 6-((dichloro(4-methoxyphenyl)-λ4-tellanyl)methyl)-5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-1-ium chlorides and annulation of the thiazoline cycle. The introduction of aryl and heteryl substituents of different nature does not affect the regioselectivity of the heteroannulation process.
|
| publisher |
V.I.Vernadsky Institute of General and Inorganic Chemistry |
| publishDate |
2023 |
| url |
https://ucj.org.ua/index.php/journal/article/view/578 |
| work_keys_str_mv |
AT oniskomikhailo aryltellurochlorinationof5arylheterylsubstitutednallyl124triazole3thionederivatives AT kutmykola aryltellurochlorinationof5arylheterylsubstitutednallyl124triazole3thionederivatives AT sukharevserhii aryltellurochlorinationof5arylheterylsubstitutednallyl124triazole3thionederivatives AT lendelvasyl aryltellurochlorinationof5arylheterylsubstitutednallyl124triazole3thionederivatives |
| first_indexed |
2025-09-24T17:43:52Z |
| last_indexed |
2025-09-24T17:43:52Z |
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1849658129327849472 |