The construction of a novel class of indazolo[2,1-a]cinnolin-7-ium and diazabenzofluoranthenium salts was developed by using Rh(iii)-catalyzed C-H activation/annulation reactions with 2-phenyl-2H-indazole, and internal alkynes, which resulted in structurally important polycyclic heteroaromatic compounds (PHAs). This reaction uses mild reaction conditions and has a high efficiency, low catalyst loading, and wide substrate scope. The overall catalytic process involves C-H activation followed by C-C/C-N bond formation. Furthermore, the synthesised cinnolinium/fluoranthenium salts exhibit potential fluorescence properties and 5i was targeted in particular for specific mitochondrial staining in order to investigate cancer cell lines.
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http://dx.doi.org/10.1039/d1ob00376c | DOI Listing |
Chem Sci
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University Chongqing 401331 P. R. China
Reported herein is the first example of a ruthenium-catalyzed C-H activation/annulation of phenothiazine-3-carbaldehydes to construct structurally diverse pyrido[3,4-]phenothiazin-3-iums with dual-emission characteristics. Novel organic single-molecule white-light materials based on pyrido[3,4-]phenothiazin-3-iums with dual-emission and thermally activated delayed fluorescence (TADF) characteristics have been developed for the first time herein. Furthermore, the dual-emission molecule could be fabricated as water-dispersed NPs, which could be applied in two-channel emission intensity ratio imaging to observe the intercellular structure and can specifically target the cell membrane.
View Article and Find Full Text PDFChem Asian J
December 2024
Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, Tamilnadu, India.
We disclosed an efficient protocol for regioselective C6 C-H/N-H activation/annulation reaction of indole-7-carboxamides with alkynes to synthesize highly substituted pyrrolo[3,2-h]isoquinolin-9-one derivatives. Under optimized reaction conditions, electron-deficient and electron-rich internal alkynes reacted efficiently with various indole-7-carboxamides to deliver desired products in good to excellent yields. The synthetic utility of the product is demonstrated by its selective oxidation to the corresponding isatin derivative.
View Article and Find Full Text PDFOrg Lett
December 2024
Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu, China.
Chem Commun (Camb)
October 2024
Wöhler Research Institute for Sustainable Chemistry (WISCh), Georg-August-Universität Göttingen, 37077, Göttingen, Germany.
Alkyne annulation represents a versatile and powerful strategy for the assembly of structurally complex compounds. Recent advances successfully enabled electrocatalytic alkyne annulations, significantly expanding the potential applications of this promising technique towards sustainable synthesis. The metallaelectro-catalyzed C-H activation/annulation stands out as a highly efficient approach that leverages electricity, combining the benefits of electrosynthesis with the power of transition-metal catalyzed C-H activation.
View Article and Find Full Text PDFNat Commun
September 2024
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, People's Republic of China.
Acenaphthylene-containing polycyclic aromatic hydrocarbons (AN-PAHs) are noteworthy structural motifs for organic functional materials due to their non-alternant electronic structure, which increases electron affinity. However, the synthesis of AN-PAHs has traditionally required multiple sequential synthetic steps, limiting structural diversity. Herein, we present a tandem C-H penta- and hexaannulation reaction of aryl alkyl ketone with acetylenedicarboxylate.
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