An efficient one-pot method is described for the highly regioselective synthesis of α-ketoamide -arylpyrazoles from secondary β-enamino diketones. For this, the key intermediate, 4-acyl 3,5-dihydroxypyrrolone, was generated in situ and underwent bimolecular nucleophilic substitution at C-5 by arylhydrazine, with subsequent heterocyclization at the carbonyl carbon of the acyl group. This strategy allowed for regiochemical control of α-ketoamide -arylpyrazoles from β-enamino diketones and arylhydrazines.
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http://dx.doi.org/10.1021/acs.orglett.9b02206 | DOI Listing |
Org Lett
January 2025
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, China.
A modular synthesis method for 1,4-diketones has been developed. Utilizing inexpensive carboxylic acid esters as carbonyl sources and tetraborylethane () as a nucleophilic reagent, a one-pot strategy for constructing two C-C bonds was established. Notably, this reaction proceeds without the involvement of transition metals and exhibits excellent functional group compatibility.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
We describe a stereoselective synthesis of the dimeric diazofluorene , a potential precursor to the cytotoxic -symmetric bacterial metabolite (-)-lomaiviticin A (). An efficient route was developed to convert the tetracyclic diol to the diketone (five steps, 30% overall). Oxidative dimerization of the enoxysilane provided the -symmetric dimeric diazofluorene in 56% yield and with 15:1:0 diastereoselectivity.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
School of Life Science and Engineering, School of Chemistry, Southwest Jiaotong University, Chengdu, 610031, China.
Under mild visible light conditions, formates facilitate C-O cleavage the EDA complex and SCS strategy, yielding α-carbonyl alkyl radicals. These radicals then react with olefins under air conditions, leading to the synthesis of diaryl 1,4-dicarbonyl compounds. Mechanistic studies reveal that α-formyloxy ketone is generated by the reaction between α-brominated acetophenone and formates, followed by the formation of the EDA complex.
View Article and Find Full Text PDFJ Phys Chem Lett
January 2025
College of Chemistry, Beijing Normal University, Beijing 100875, P. R. China.
Long-range exciton transport is crucial for optoelectronic devices based on organic semiconductors, but the method for increasing and regulating the exciton transport rate in organic semiconductors is still underexplored. Here we have achieved rapid-transporting excitons in organic crystals assembled of difluoroboron β-diketonate (BCZ) and found that the exciton transport rate of BCZ crystals can be regulated by the molecular packing form. Using transient absorption microscopy, we find that the BCZ-Y crystal in which BCZ molecules experience uniform head-to-tail antiparallel molecular packing has anisotropic long-range exciton transport.
View Article and Find Full Text PDFNat Commun
January 2025
State Key Laboratory of Organometallic Chemistry and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, People's Republic of China.
Transparent wood with high transmittance and versatility has attracted great attention as an energy-saving building material. Many studies have focused on luminescent transparent wood, while the research on organic afterglow transparent wood is an interesting combination. Here, we use luminescent difluoroboron β-diketonate (BFbdk) compounds, methyl methacrylate (MMA), delignified wood, and initiators to prepare room-temperature phosphorescent transparent wood by thermal initiation polymerization.
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