Design, synthesis and structure of novel dendritic G-2 melamines comprising piperidine motifs as key linkers and 4-(n-octyloxy)aniline as a peripheral unit
| Autor: | Cristina Morar, Gabriel Katona, Attila Bende, Dan Porumb, Emese Gal, Alexandru Lupan, Dominique Harakat, Radu Silaghi-Dumitrescu, Pedro Lameiras, Mircea Darabantu, Carmen Sacalis |
|---|---|
| Přispěvatelé: | Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
[CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Cyanuric chloride Dendritic melamines Cyclohexylamine 010402 general chemistry 01 natural sciences Biochemistry Nano-aggregates 0104 chemical sciences chemistry.chemical_compound Crystallography Aniline chemistry Dendrimer 4-(n-Octyloxy)aniline Drug Discovery Reactivity (chemistry) Density functional theory Piperidine 4-Aminopiperidine Amination |
| Zdroj: | Tetrahedron Tetrahedron, Elsevier, 2019, 75 (35), pp.130468. ⟨10.1016/j.tet.2019.130468⟩ |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2019.130468⟩ |
| Popis: | International audience; Starting from 4-amino-1-(tert-butoxycarbonyl)piperidine (Boc-PD-NH2), we report the synthesis of three novel meta-tri- and dimeric tetravalent N-substituted melamines with piperidin-4-yl groups. These compounds were used as central building-blocks and successfully incorporated into three new G-2 melamine dendrimers containing 4-(n-octyloxy)aniline as a peripheral unit. From a structural point of view, the challenging reactivity of Boc-PD-NH2 in comparison with 1-Boc-piperazine and cyclohexylamine, as SN2-Ar amination reagents against cyanuric chloride, was interpreted in terms of DFT (Density Functional Theory) thermodynamic and electronic computed data. Two out of the three dendrimers self-assembled in the solid state as large homogeneously packed spherical nano-aggregates (average D values ranging between 2500 and 3200 nm, TEM (Transmission Electron Microscopy) data) as a result of their “shell-to-shell” pre-associations in solution (DMF and 1,4-dioxane), promoted by chiral self-organisation, “round”- or “oval”-vaulted shapes (DFT data). |
| Databáze: | OpenAIRE |
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