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Synthesis 2022; 54(07): 1803-1816
DOI: 10.1055/a-1700-3115
DOI: 10.1055/a-1700-3115
paper
An Experimental and Theoretical Study of the 1,3-Dipolar Cycloaddition of Alloxan-Derived Azomethine Ylides to Cyclopropenes
The authors are grateful for the financial support from the Russian Science Foundation (RSF 20-15-00332).
Abstract
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.
Key words
1,3-dipolar cycloaddition - azomethine ylides - cyclopropenes - alloxan - one-pot, three-component reactions - spirobarbiturates - diastereoselectivity - DFT calculationsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1700-3115.
- Supporting Information
- CIF File
Publikationsverlauf
Eingereicht: 15. Oktober 2021
Angenommen nach Revision: 17. November 2021
Accepted Manuscript online:
17. November 2021
Artikel online veröffentlicht:
16. Dezember 2021
© 2021. Thieme. All rights reserved
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