Design of novel catalysts for synthesis of 1,5-benzodiazepines from 1,2-phenylenediamine and ketones: NH2-MIL-101(Al) as integrated structural scaffold for catalytic materials based on calix[4]arenes.
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| Title: | Design of novel catalysts for synthesis of 1,5-benzodiazepines from 1,2-phenylenediamine and ketones: NH2-MIL-101(Al) as integrated structural scaffold for catalytic materials based on calix[4]arenes. |
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| Authors: | Isaeva, Vera I.1 sharf@ioc.ac.ru, Timofeeva, Maria N.1 timofeeva@catalysis.ru, Panchenko, Valentina N.1, Lukoyanov, Ivan A.1, Chernyshev, Vladimir V.1, Kapustin, Gennady I.1, Davshan, Nikolai A.1, Kustov, Leonid M.1 |
| Source: | Journal of Catalysis. Jan2019, Vol. 369, p60-71. 12p. |
| Subjects: | Benzodiazepines, Phenylenediamines, Ketones, Aromatic compounds, Catalysts |
| Abstract: | Graphical abstract Highlights • NH 2 -MIL-101(Al) was used as a scaffold for synthesis of novel catalysts based on calix[4]arenes. • para -Sulfonatocalix[4]arene and para -tert-butylthiacalix[4]arene with CN groups were used. • Ship in a bottle approach was used for microwave assisted one-step synthesis of composites. • Efficiency of composite materials was investigated in the synthesis of 1,5-benzodiazepines. • The host-guest interaction affects the physicochemical and catalytic properties of composites. Abstract Novel nanoporous composites (MIL/K-SO 3 H and MIL/Ks-CN) were synthesized by the encapsulation of para -sulfonatocalix[4]arene (K-SO 3 H) and para -tert-butylthiacalix[4]arene (Ks-CN) with strong (SO 3 H) and weak (CN) acidic functionalities, respectively, in the aluminum(III) 2-aminoterephthalate metal organic framework (NH 2 -MIL-101(Al)) cavities. MIL/K-SO 3 H and MIL/Ks-CN materials were prepared by microwave assisted one-step synthesis in situ following to the ship in a bottle approach. According to comprehensive study, textural properties, the morphology and particle sizes of composites depend on the type of the embedded calix[4]arene molecules. Catalytic properties of MIL/K-SO 3 H and MIL/Ks-CN composites were investigated in the synthesis of physiologically active 1,5-benzodiazepines from 1,2-phenylenediamine and ketones (acetone, acetophenone, methyl ethyl ketone). It was found that their catalytic activity can be adjusted by surface acidity, which depends on the nature of the interactions between functional substituents in the arene "bowl" of calix[4]arenes and NH 2 groups in organic linkers of NH 2 -MIL-101(Al) framework. [ABSTRACT FROM AUTHOR] |
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| Database: | Engineering Source |
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