Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidine-7-ones by one-step Vorbrüggen glycosylation
New analogues of acyclovir have been prepared by reacting 1,2,4-triazolo[1,5-a]pyrimidin-7-ones 1а-i and (2-acetoxyethoxy)methyl acetate 2 in the presence of trimethylsilyl trifluoromethanesulfonate as a catalyst. Thei nteraction between the compounds 1а-е and 2 has led to a mixture of N3 and N4 iso...
Saved in:
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Ural Federal University
2015-05-01
|
| Series: | Chimica Techno Acta |
| Subjects: | |
| Online Access: | https://chimicatechnoacta.ru/article/view/1126 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849304641883340800 |
|---|---|
| author | I. A. Khalymbadzha S. L. Deev T. S. Shestakova V. L. Rusinov O. N. Chupakhin |
| author_facet | I. A. Khalymbadzha S. L. Deev T. S. Shestakova V. L. Rusinov O. N. Chupakhin |
| author_sort | I. A. Khalymbadzha |
| collection | DOAJ |
| description | New analogues of acyclovir have been prepared by reacting 1,2,4-triazolo[1,5-a]pyrimidin-7-ones 1а-i and (2-acetoxyethoxy)methyl acetate 2 in the presence of trimethylsilyl trifluoromethanesulfonate as a catalyst. Thei nteraction between the compounds 1а-е and 2 has led to a mixture of N3 and N4 isomers. In contrast, the reaction of compounds 1g-i and 2 proceeded selectively to form N3 isomers. In the case of compounds 1a-c the predominant product is the one with the acyclic moiety in azine ring (N4 isomer). Interaction between 1d-f and 2 has led to mixtures comprising mainly N3 isomer. It has been found that the ratio of glycosylation products 1 and 2 are thermodynamically controlled. The structure of the obtained compounds has been proved by 1Н, 13С, two-dimensional 1Н-13С NMR spectroscopy and X-ray analysis. |
| format | Article |
| id | doaj-art-417bf516e5d54639ab869d7f7d88b5ed |
| institution | Kabale University |
| issn | 2411-1414 |
| language | English |
| publishDate | 2015-05-01 |
| publisher | Ural Federal University |
| record_format | Article |
| series | Chimica Techno Acta |
| spelling | doaj-art-417bf516e5d54639ab869d7f7d88b5ed2025-08-20T03:55:40ZengUral Federal UniversityChimica Techno Acta2411-14142015-05-012215816310.15826/chimtech.2015.2.2.0171242Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidine-7-ones by one-step Vorbrüggen glycosylationI. A. Khalymbadzha0S. L. Deev1T. S. Shestakova2V. L. Rusinov3O. N. Chupakhin4Институт органического синтеза УрО РАН, ЕкатеринбургИнститут органического синтеза УрО РАН, ЕкатеринбургИнститут органического синтеза УрО РАН, ЕкатеринбургИнститут органического синтеза УрО РАН, ЕкатеринбургИнститут органического синтеза УрО РАН, ЕкатеринбургNew analogues of acyclovir have been prepared by reacting 1,2,4-triazolo[1,5-a]pyrimidin-7-ones 1а-i and (2-acetoxyethoxy)methyl acetate 2 in the presence of trimethylsilyl trifluoromethanesulfonate as a catalyst. Thei nteraction between the compounds 1а-е and 2 has led to a mixture of N3 and N4 isomers. In contrast, the reaction of compounds 1g-i and 2 proceeded selectively to form N3 isomers. In the case of compounds 1a-c the predominant product is the one with the acyclic moiety in azine ring (N4 isomer). Interaction between 1d-f and 2 has led to mixtures comprising mainly N3 isomer. It has been found that the ratio of glycosylation products 1 and 2 are thermodynamically controlled. The structure of the obtained compounds has been proved by 1Н, 13С, two-dimensional 1Н-13С NMR spectroscopy and X-ray analysis.https://chimicatechnoacta.ru/article/view/1126аналоги ацикловира |
| spellingShingle | I. A. Khalymbadzha S. L. Deev T. S. Shestakova V. L. Rusinov O. N. Chupakhin Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidine-7-ones by one-step Vorbrüggen glycosylation Chimica Techno Acta аналоги ацикловира |
| title | Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidine-7-ones by one-step Vorbrüggen glycosylation |
| title_full | Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidine-7-ones by one-step Vorbrüggen glycosylation |
| title_fullStr | Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidine-7-ones by one-step Vorbrüggen glycosylation |
| title_full_unstemmed | Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidine-7-ones by one-step Vorbrüggen glycosylation |
| title_short | Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidine-7-ones by one-step Vorbrüggen glycosylation |
| title_sort | synthesis of acyclic nucleoside analogues based on 1 2 4 triazolo 1 5 a pyrimidine 7 ones by one step vorbruggen glycosylation |
| topic | аналоги ацикловира |
| url | https://chimicatechnoacta.ru/article/view/1126 |
| work_keys_str_mv | AT iakhalymbadzha synthesisofacyclicnucleosideanaloguesbasedon124triazolo15apyrimidine7onesbyonestepvorbruggenglycosylation AT sldeev synthesisofacyclicnucleosideanaloguesbasedon124triazolo15apyrimidine7onesbyonestepvorbruggenglycosylation AT tsshestakova synthesisofacyclicnucleosideanaloguesbasedon124triazolo15apyrimidine7onesbyonestepvorbruggenglycosylation AT vlrusinov synthesisofacyclicnucleosideanaloguesbasedon124triazolo15apyrimidine7onesbyonestepvorbruggenglycosylation AT onchupakhin synthesisofacyclicnucleosideanaloguesbasedon124triazolo15apyrimidine7onesbyonestepvorbruggenglycosylation |