DC pole | Wartość | Język |
dc.contributor.author | Wantulok, Jakub | - |
dc.contributor.author | Szala, Marcin | - |
dc.contributor.author | Quinto, Andrea | - |
dc.contributor.author | Nycz, Jacek E. | - |
dc.contributor.author | Giannarelli, Stefania | - |
dc.contributor.author | Sokolová, Romana | - |
dc.contributor.author | Książek, Maria | - |
dc.contributor.author | Kusz, Joachim | - |
dc.date.accessioned | 2020-04-29T12:32:06Z | - |
dc.date.available | 2020-04-29T12:32:06Z | - |
dc.date.issued | 2020 | - |
dc.identifier.citation | Molecules, 2020, iss. 9, art. no. 2053 | pl_PL |
dc.identifier.issn | 1420-3049 | - |
dc.identifier.uri | http://hdl.handle.net/20.500.12128/13731 | - |
dc.description.abstract | A new approach to the synthesis of selected quinolinecarbaldehydes with carbonyl groups located at C5 and/or in C7 positions is presented in this paper in conjunction with spectroscopic characterization of the products. The classical Reimer-Tiemann, Vilsmeier-Haack and Duff aldehyde synthesis methods were compared due to their importance. Computational studies were carried out to explain the preferred selectivity of the presented formylation transformations. A carbene insertion reaction based on Reimer-Tiemann methodology is presented for making 7-bromo-8-hydroxyquinoline-5-carbaldehyde. Additionally, Duff and Vilsmeier-Haack reactions were used in the double formylation of quinoline derivatives and their analogues benzo[h]quinolin-10-ol, 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde, 8-(dimethylamino) quinoline-5,7-dicarbaldehyde and 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde. Four Schiff base derivatives of 2,6-diisopropylbenzenamine were prepared from selected quinoline-5-carbaldehydes and quinoline-7-carbaldehyde by an efficient synthesis protocol. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, FTIR, electronic absorption spectroscopy and multinuclear NMR. The electrochemical properties of 8-hydroxy-quinoline-5-carbaldehyde, 6-(dimethylamino)quinoline-5-carbaldehyde and its methylated derivative were investigated, and a strong correlation between the chemical structure and obtained reduction and oxidation potentials was found. The presence of a methyl group facilitates oxidation. In contrast, the reduction potential of methylated compounds was more negative comparing to non-methylated structure. Calculations of frontier molecular orbitals supported the finding. The structures of 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde and four Schiff bases were determined by single-crystal X-ray diffraction measurements. | pl_PL |
dc.language.iso | en | pl_PL |
dc.rights | Uznanie autorstwa 3.0 Polska | * |
dc.rights.uri | http://creativecommons.org/licenses/by/3.0/pl/ | * |
dc.subject | vilsmeier-haack | pl_PL |
dc.subject | reimer-tiemann | pl_PL |
dc.subject | duff | pl_PL |
dc.subject | aldehyde | pl_PL |
dc.subject | aldazine | pl_PL |
dc.subject | heterocyclic | pl_PL |
dc.subject | cyclic voltammetry | pl_PL |
dc.title | Synthesis, electrochemical and spectroscopic characterization of selected quinolinecarbaldehydes and their Schiff base derivatives | pl_PL |
dc.type | info:eu-repo/semantics/article | pl_PL |
dc.relation.journal | Molecules | pl_PL |
dc.identifier.doi | 10.3390/molecules25092053 | - |
Pojawia się w kolekcji: | Artykuły (WNŚiT)
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