Revisiting Fused‐Pyrrolo‐1,10‐Phenanthroline Derivatives: Novel Transformations and Stability Studies
Cristina M. Al Matarneh, Alina Nicolescu, Sergiu Shova, Mircea Apostu, Razvan Puf, Francesca Mocci, Aatto Laaksonen, Ionel I. Mangalagiu, Ramona Danac
TL;DR
This paper explores the synthesis and stability of new fused-pyrrolo-1,10-phenanthroline compounds, revealing how different chemical groups affect their behavior.
Contribution
The study introduces novel synthetic methods and stability insights for fused-pyrrolo-1,10-phenanthroline derivatives.
Findings
Electron-donating groups in the para position of the phenyl ring promote easier oxidation.
Electron-withdrawing substituents enhance the stability of the compounds.
Unexpected transformations occur during the synthesis of the derivatives.
Abstract
In this study, new pyrrolo[3',4':3,4]pyrrolo[1,2‐a][1,10]phenanthroline derivatives are developed and their stabilities and transformation pathways are investigated. The synthetic approach toward these novel derivatives include a pivotal [3 + 2] cycloaddition of in situ generated ylides, followed by cycloadducts oxidation and other unexpected transformations. The structures of the intermediate and final compounds are proposed based on information obtained from several spectral techniques. Stability study reveal that electron‐donating groups in the para position of the phenyl ring promote easier oxidation, whereas electron‐withdrawing substituents enhance the stability of the compounds. The acid–base titration of α‐monosubstituted 1,10‐phenanthroline 6a results in a reversible color change, which is preliminarily explored through spectral methods. The synthesis of new…
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Taxonomy
TopicsSynthesis and Reactivity of Heterocycles · Catalytic Cross-Coupling Reactions · Magnetism in coordination complexes