期刊
ACS APPLIED MATERIALS & INTERFACES
卷 12, 期 20, 页码 23002-23009出版社
AMER CHEMICAL SOC
DOI: 10.1021/acsami.0c05344
关键词
tandem reaction; metal-organic frameworks; hierarchical pore; heterogeneous catalysis; bioactivity; quinoline N-oxides
资金
- Iowa State University
- National Key R&D Program of China [2016YFA0202900]
- National Natural Science Foundation of China [21878266, 21722609]
- National Science Foundation (NSF) [CHE-1566445]
- U.S. Department of Energy (DOE), Office of Basic Energy Sciences, Division of Chemical Sciences, Geosciences, and Biosciences
- U.S. DOE [DE-AC02-07CH11358]
Multifunctional metal-organic frameworks (MOFs) that possess permanent porosity are promising catalysts in organic transformation. Herein, we report the construction of a hierarchical MOF functionalized with basic aliphatic amine groups and polyvinylpyrrolidone-capped platinum nanoparticles (Pt NPs). The postsynthetic covalent modification of organic ligands increases basic site density in the MOF and simultaneously introduces mesopores to create a hierarchically porous structure. The multifunctional MOF is capable of catalyzing a sequential Knoevenagel condensation-hydrogenation-intramolecular cyclization reaction. The unique selective reduction of the nitro group to intermediate hydroxylamine by Pt NPs supported on MOF followed by intramolecular cyclization with a cyano group affords an excellent yield (up to 92%) to the uncommon quinoline N-oxides over quinolines. The hierarchical MOF and polyvinylpyrrolidone capping agent on Pt NPs synergistically facilitate the enrichment of substrates and thus lead to high activity in the reduction-intramolecular cyclization reaction. The bioactivity assay indicates that the synthesized quinoline N-oxides evidently inhibit the proliferation of lung cancer cells. Our findings demonstrate the feasibility of MOF-catalyzed direct synthesis of bioactive molecules from readily available compounds under mild conditions.
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