Duff Aldehyde Synthesis

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Kusz Joachim - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis, electrochemical and spectroscopic characterization of selected quinolinecarbAldehydes and their Schiff base derivatives
    'MDPI AG', 2020
    Co-Authors: Wantulok Jakub, Szala Marcin, Quinto Andrea, Nycz, Jacek E., Giannarelli Stefania, Sokolová Romana, Książek Maria, Kusz Joachim
    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

Wantulok Jakub - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis, electrochemical and spectroscopic characterization of selected quinolinecarbAldehydes and their Schiff base derivatives
    'MDPI AG', 2020
    Co-Authors: Wantulok Jakub, Szala Marcin, Quinto Andrea, Nycz, Jacek E., Giannarelli Stefania, Sokolová Romana, Książek Maria, Kusz Joachim
    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

Szala Marcin - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis, electrochemical and spectroscopic characterization of selected quinolinecarbAldehydes and their Schiff base derivatives
    'MDPI AG', 2020
    Co-Authors: Wantulok Jakub, Szala Marcin, Quinto Andrea, Nycz, Jacek E., Giannarelli Stefania, Sokolová Romana, Książek Maria, Kusz Joachim
    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

Quinto Andrea - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis, electrochemical and spectroscopic characterization of selected quinolinecarbAldehydes and their Schiff base derivatives
    'MDPI AG', 2020
    Co-Authors: Wantulok Jakub, Szala Marcin, Quinto Andrea, Nycz, Jacek E., Giannarelli Stefania, Sokolová Romana, Książek Maria, Kusz Joachim
    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

Nycz, Jacek E. - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis, electrochemical and spectroscopic characterization of selected quinolinecarbAldehydes and their Schiff base derivatives
    'MDPI AG', 2020
    Co-Authors: Wantulok Jakub, Szala Marcin, Quinto Andrea, Nycz, Jacek E., Giannarelli Stefania, Sokolová Romana, Książek Maria, Kusz Joachim
    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