Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions
Nucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-01-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2023/1/M1551 |
| _version_ | 1827748420108943360 |
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| author | Roman D. Marchenko Andrei S. Potapov |
| author_facet | Roman D. Marchenko Andrei S. Potapov |
| author_sort | Roman D. Marchenko |
| collection | DOAJ |
| description | Nucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2-yl)alkanes were the dominating products, while bis(triazol-1-yl)alkanes were detected only in trace amounts. The same products could also be obtained under solvent-free conditions in a neat reaction mixture. The proposed methods are economically feasible, do not require using toxic solvents or catalysts, and make the (1,2,3-triazol-2-yl)-derivatives, inaccessible by alkyne-azide cycloaddition (click) reactions, readily available. |
| first_indexed | 2024-03-11T06:08:00Z |
| format | Article |
| id | doaj.art-13f60aa1c17742f19b4d0ad1cf6d9cb8 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-11T06:08:00Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-13f60aa1c17742f19b4d0ad1cf6d9cb82023-11-17T12:49:18ZengMDPI AGMolbank1422-85992023-01-0120231M155110.3390/M1551Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free ConditionsRoman D. Marchenko0Andrei S. Potapov1Kizhner Research Center, National Research Tomsk Polytechnic University, 30 Lenin Ave., 634050 Tomsk, RussiaNikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, 3 Lavrentiev Ave., 630090 Novosibirsk, RussiaNucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2-yl)alkanes were the dominating products, while bis(triazol-1-yl)alkanes were detected only in trace amounts. The same products could also be obtained under solvent-free conditions in a neat reaction mixture. The proposed methods are economically feasible, do not require using toxic solvents or catalysts, and make the (1,2,3-triazol-2-yl)-derivatives, inaccessible by alkyne-azide cycloaddition (click) reactions, readily available.https://www.mdpi.com/1422-8599/2023/1/M15511,2,3-triazolebis(1,2,3-triazol-2-yl)methane1,2-bis(1,2,3-triazol-2-yl)ethanenucleophilic substitutionsolvent-free synthesissuperbasic medium |
| spellingShingle | Roman D. Marchenko Andrei S. Potapov Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions Molbank 1,2,3-triazole bis(1,2,3-triazol-2-yl)methane 1,2-bis(1,2,3-triazol-2-yl)ethane nucleophilic substitution solvent-free synthesis superbasic medium |
| title | Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions |
| title_full | Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions |
| title_fullStr | Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions |
| title_full_unstemmed | Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions |
| title_short | Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions |
| title_sort | synthesis of bis 1 2 3 triazolyl alkanes in superbasic and solvent free conditions |
| topic | 1,2,3-triazole bis(1,2,3-triazol-2-yl)methane 1,2-bis(1,2,3-triazol-2-yl)ethane nucleophilic substitution solvent-free synthesis superbasic medium |
| url | https://www.mdpi.com/1422-8599/2023/1/M1551 |
| work_keys_str_mv | AT romandmarchenko synthesisofbis123triazolylalkanesinsuperbasicandsolventfreeconditions AT andreispotapov synthesisofbis123triazolylalkanesinsuperbasicandsolventfreeconditions |