1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles
A new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in SNAr reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. T...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2021-02-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.17.37 |
| _version_ | 1818725577927950336 |
|---|---|
| author | Dace Cīrule Irina Novosjolova Ērika Bizdēna Māris Turks |
| author_facet | Dace Cīrule Irina Novosjolova Ērika Bizdēna Māris Turks |
| author_sort | Dace Cīrule |
| collection | DOAJ |
| description | A new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in SNAr reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C–O and C–C bond forming reactions clearly show the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as leaving group. |
| first_indexed | 2024-12-17T21:44:32Z |
| format | Article |
| id | doaj.art-f5d0795e91be4510962ae8f6229aa122 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T21:44:32Z |
| publishDate | 2021-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-f5d0795e91be4510962ae8f6229aa1222022-12-21T21:31:30ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-02-0117141041910.3762/bjoc.17.371860-5397-17-371,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophilesDace Cīrule0Irina Novosjolova1Ērika Bizdēna2Māris Turks3Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaFaculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaFaculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaFaculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaA new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in SNAr reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C–O and C–C bond forming reactions clearly show the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as leaving group.https://doi.org/10.3762/bjoc.17.372,6-bistriazolyl purinesnucleophilic aromatic substitutionpurine nucleosidestriazoles |
| spellingShingle | Dace Cīrule Irina Novosjolova Ērika Bizdēna Māris Turks 1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles Beilstein Journal of Organic Chemistry 2,6-bistriazolyl purines nucleophilic aromatic substitution purine nucleosides triazoles |
| title | 1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles |
| title_full | 1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles |
| title_fullStr | 1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles |
| title_full_unstemmed | 1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles |
| title_short | 1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles |
| title_sort | 1 2 3 triazoles as leaving groups snar reactions of 2 6 bistriazolylpurines with o and c nucleophiles |
| topic | 2,6-bistriazolyl purines nucleophilic aromatic substitution purine nucleosides triazoles |
| url | https://doi.org/10.3762/bjoc.17.37 |
| work_keys_str_mv | AT dacecirule 123triazolesasleavinggroupssnarreactionsof26bistriazolylpurineswithoandcnucleophiles AT irinanovosjolova 123triazolesasleavinggroupssnarreactionsof26bistriazolylpurineswithoandcnucleophiles AT erikabizdena 123triazolesasleavinggroupssnarreactionsof26bistriazolylpurineswithoandcnucleophiles AT maristurks 123triazolesasleavinggroupssnarreactionsof26bistriazolylpurineswithoandcnucleophiles |