Catalyst-free synthesis of various derivatives of a novel heterocyclic system of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine
Azolo-annulated pyrimidines have attracted continuing interest due primarily to their structural similarity to heterocyclic bases of DNA and RNA. As a consequence, these compounds can act as antimetabolites, being effective biologically active compounds. Numerous advantageous properties of azolopyri...
| الحاوية / القاعدة: | شیمی کاربردی روز |
|---|---|
| المؤلفون الرئيسيون: | , , , |
| التنسيق: | مقال |
| اللغة: | الإنجليزية |
| منشور في: |
Semnan University
2022-09-01
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| الموضوعات: | |
| الوصول للمادة أونلاين: | https://chemistry.semnan.ac.ir/article_7151_9c5405148047f6d6239292e25c67e66a.pdf |
| _version_ | 1850366501520932864 |
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| author | Niloufar Dindar-Fouladlu Seddigheh Sheikhi-Mohammareh Kayvan Saadat Ali Shiri |
| author_facet | Niloufar Dindar-Fouladlu Seddigheh Sheikhi-Mohammareh Kayvan Saadat Ali Shiri |
| author_sort | Niloufar Dindar-Fouladlu |
| collection | DOAJ |
| container_title | شیمی کاربردی روز |
| description | Azolo-annulated pyrimidines have attracted continuing interest due primarily to their structural similarity to heterocyclic bases of DNA and RNA. As a consequence, these compounds can act as antimetabolites, being effective biologically active compounds. Numerous advantageous properties of azolopyrimidines such as important industrial, agrochemical and pharmaceutical applications, especially in biological science, material chemistry and medicinal chemistry impelled us to design and synthesis of a number of various and interesting derivatives of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine as a novel heterocyclic system which has not been reported previously. In the present work, initially the reaction of 2,4-dichloro-6-methylpyrimidin-5-amine (1) with different primary amines in refluxing i-PrOH gave the corresponding sec-amino derivatives (2a-e) which were consequently treated with NaNO2/HCl solution to yield quantitatively the corresponding diazo derivatives of 5-chloro-3-alkyl-7-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (3a-e). Further reaction of compounds (3a-e) with NaN3 in EtOH was resulted in various derivatives of novel heterocyclic system of tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine (4a-e) that are in equilibrium with azide forms. |
| format | Article |
| id | doaj-art-05fd00a48a83459eae50dca2cefb428b |
| institution | Directory of Open Access Journals |
| issn | 2981-2437 |
| language | English |
| publishDate | 2022-09-01 |
| publisher | Semnan University |
| record_format | Article |
| spelling | doaj-art-05fd00a48a83459eae50dca2cefb428b2025-08-19T23:03:11ZengSemnan Universityشیمی کاربردی روز2981-24372022-09-01176418920410.22075/chem.2022.25003.20207151Catalyst-free synthesis of various derivatives of a novel heterocyclic system of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidineNiloufar Dindar-Fouladlu0Seddigheh Sheikhi-Mohammareh1Kayvan Saadat2Ali Shiri3Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, IranDepartment of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, IranDepartment of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, IranDepartment of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, IranAzolo-annulated pyrimidines have attracted continuing interest due primarily to their structural similarity to heterocyclic bases of DNA and RNA. As a consequence, these compounds can act as antimetabolites, being effective biologically active compounds. Numerous advantageous properties of azolopyrimidines such as important industrial, agrochemical and pharmaceutical applications, especially in biological science, material chemistry and medicinal chemistry impelled us to design and synthesis of a number of various and interesting derivatives of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine as a novel heterocyclic system which has not been reported previously. In the present work, initially the reaction of 2,4-dichloro-6-methylpyrimidin-5-amine (1) with different primary amines in refluxing i-PrOH gave the corresponding sec-amino derivatives (2a-e) which were consequently treated with NaNO2/HCl solution to yield quantitatively the corresponding diazo derivatives of 5-chloro-3-alkyl-7-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (3a-e). Further reaction of compounds (3a-e) with NaN3 in EtOH was resulted in various derivatives of novel heterocyclic system of tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine (4a-e) that are in equilibrium with azide forms.https://chemistry.semnan.ac.ir/article_7151_9c5405148047f6d6239292e25c67e66a.pdfpyrimidinetriazolopyrimidinetetrazolotriazolopyrimidinetetrazole-azide equilibrium |
| spellingShingle | Niloufar Dindar-Fouladlu Seddigheh Sheikhi-Mohammareh Kayvan Saadat Ali Shiri Catalyst-free synthesis of various derivatives of a novel heterocyclic system of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine pyrimidine triazolopyrimidine tetrazolotriazolopyrimidine tetrazole-azide equilibrium |
| title | Catalyst-free synthesis of various derivatives of a novel heterocyclic system of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine |
| title_full | Catalyst-free synthesis of various derivatives of a novel heterocyclic system of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine |
| title_fullStr | Catalyst-free synthesis of various derivatives of a novel heterocyclic system of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine |
| title_full_unstemmed | Catalyst-free synthesis of various derivatives of a novel heterocyclic system of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine |
| title_short | Catalyst-free synthesis of various derivatives of a novel heterocyclic system of 3-alkyl-9-methyl-tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine |
| title_sort | catalyst free synthesis of various derivatives of a novel heterocyclic system of 3 alkyl 9 methyl tetrazolo 1 5 a 1 2 3 triazolo 4 5 d pyrimidine |
| topic | pyrimidine triazolopyrimidine tetrazolotriazolopyrimidine tetrazole-azide equilibrium |
| url | https://chemistry.semnan.ac.ir/article_7151_9c5405148047f6d6239292e25c67e66a.pdf |
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