An Experimental and Theoretical Study of the 1,3-Dipolar Cycloaddition of Alloxan-Derived Azomethine Ylides to Cyclopropenes
| Autor: | Anna G. Larina, S. V. Shmakov, Vitali M. Boitsov, Alexander S. Filatov, Stanislav I. Selivanov, Alexander V. Stepakov |
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| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | Synthesis. 54:1803-1816 |
| ISSN: | 1437-210X 0039-7881 |
| Popis: | A diastereoselective synthesis of biologically interesting spirobarbiturates has been achieved via [3+2] cycloaddition of alloxan-derived azomethine ylides to 3-R-1,2-diphenylcyclopropenes. With this approach, a range of spirobarbiturate-3-azabicyclo[3.1.0]hexanes and spirobarbiturate-cyclopropa[a]pyrrolizines were obtained in moderate to good yields with excellent diastereoselectivities. DFT calculations (M11 density functional theory) were carried out to shed light on the molecular mechanism of 1,3-dipolar cycloaddition of alloxan-derived azomethine ylides to cyclopropenes. The cytotoxic activity of some obtained compounds against human erythroleukemia (K562) cell line was evaluated in vitro by MTS-assay. |
| Databáze: | OpenAIRE |
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