Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition
| Autor: | Vladimir I. Musatov, Maryna O Mazur, Eugene M Zviagin, Oleksii S Zhelavskyi, Elena H. Shvets, Maksim A. Kolosov, Svitlana V. Shishkina, Anna Yu Andryushchenko, Valentyn A. Chebanov |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
multicomponent reactions ugi reaction Organic Chemistry chemistry.chemical_element Alkyne Combinatorial chemistry Full Research Paper Cycloaddition Ruthenium microwave chemistry lcsh:QD241-441 Chemistry chemistry.chemical_compound chemistry Microwave chemistry triazolobenzodiazepines lcsh:Organic chemistry Intramolecular force click chemistry Click chemistry Ugi reaction lcsh:Q Azide lcsh:Science |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 17, Iss 1, Pp 678-687 (2021) Beilstein Journal of Organic Chemistry |
| ISSN: | 1860-5397 |
| Popis: | A novel catalyst-free synthetic approach to 1,2,3-triazolobenzodiazepinones has been developed and optimized. The Ugi reaction of 2-azidobenzaldehyde, various amines, isocyanides, and acids followed by microwave-assisted intramolecular azide–alkyne cycloaddition (IAAC) gave a series of target heterocyclic compounds in moderate to excellent yields. Surprisingly, the normally required ruthenium-based catalysts were found to not affect the IAAC, only making isolation of the target compounds harder while the microwave-assisted catalyst-free conditions were effective for both terminal and non-terminal alkynes. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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