ArticleBeilstein journal of organic chemistry2022
Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple.
Article in Beilstein journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed.
- Study of Cytotoxicity of Pyrrolo[3,4-International journal of molecular sciences · 2026Article
- Synthesis of heterocycles based on azomethine ylides from α-amino acids (or amines) and carbonyl compounds.Beilstein journal of organic chemistry · 2026Review
- Spirobarbiturates with a pyrrolizidine moiety: synthesis, structure and biological evaluation.Beilstein journal of organic chemistry · 2026Article
- Study of Cytotoxicity of 3-Azabicyclo[3.1.0]hexanes and Cyclopropa[International journal of molecular sciences · 2025Article
- Study of Cytotoxicity of Spiro-Fused [3-Azabicyclo[3.1.0]hexane]oxindoles and Cyclopropa[a]pyrrolizidine-oxindoles Against Tumor Cell Lines.Pharmaceuticals (Basel, Switzerland) · 2024Article
- Cycloadditions of 4-Alkenyl-2-aminothiazoles with Nitroalkenes in the Formal Synthesis of Pramipexole: An Experimental and Computational Study.The Journal of organic chemistry · 2024Article
- 11International journal of molecular sciences · 2022Article
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5 authors.
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Abstract
A reliable method for the synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexanes through the 1,3-dipolar cycloaddition (1,3-DC) reactions of cyclopropenes to the stable azomethine ylide - protonated form of Ruhemann's purple (PRP) has been developed. Both 3-substituted and 3,3-disubstituted cyclopropenes reacted with PRP, affording the corresponding bis-spirocyclic 3-azabicyclo[3.1.0]hexane cycloadducts in moderate to good yields with high diastereofacial selectivity. Moreover, several unstable 1,2-disubstituted cyclopropenes were successfully trapped by the stable 1,3-dipole under mild conditions. The mechanism of the cycloaddition reactions of cyclopropenes with PRP has been thoroughly studied using density functional theory (DFT) methods at the M11/cc-pVDZ level of theory. The cycloaddition reactions have been found to be HOMO
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