A visible-light-induced radical cyclization of α-brominated amides has been developed to construct benzimidazole[2,1-]isoquinolin-6(5)-ones and pyrrolidonesin in yields up to 97%. The methodology exhibits a certain functional-group compatibility with 43 examples and operational simplicity, offering a rapid and concise approach to obtain five- and six-membered rings under the irradiation of 18 W blue LED. Additionally, large-scale reaction of this method for synthesizing benzimidazo-isoquinolineones and the further transformations to useful pyrrolidones were also conducted and afforded positive results.
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http://dx.doi.org/10.1021/acs.orglett.4c04292 | DOI Listing |
Chem Asian J
January 2025
IICT CSIR: Indian Institute of Chemical Technology, Organic Synthesis & Process Chemistry, Tarnaka, 500007, Hyderabad, INDIA.
A ferrocene-catalyzed cyanoalkylsulfonylative radical cascade cyclization of aryl 1,6-diynes using cycloketone oxime esters and DABCO.(SO₂)₂ (DABSO) is reported. The reaction proceeds with notable chemo- and regioselectivity, without requiring additional oxidants or reductants.
View Article and Find Full Text PDFChem Asian J
January 2025
Meiji Pharmaceutical University, Pharmaceutical Sciences, 2-522-1 Noshio, 204-8588, Kiyose, JAPAN.
The catalytic indirect reductive quenching method is facilitated by a combination of Ir(III) photoredox and sulfide dual-catalysis system. This study demonstrated a method for synthesizing multi-substituted furans by using a photoredox/sulfide dual-catalysis system. This method enables the synthesis of various furan derivatives, including spirofurans and phthalans.
View Article and Find Full Text PDFRSC Adv
January 2025
College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Engineering Technology Research Center of Key Preparation Technology of Biomedical Polymer Materials Changde 415000 China.
Indole-fused pyridines are an important motif in pharmaceuticals and functional molecules. A visible-light induced Ru(bpy)Cl·6HO catalyzed radical cascade sulfonylation/cyclization strategy for the synthesis of indole-fused pyridine derivatives was developed. Diverse indole-fused pyridines bearing different functional groups were obtained in moderate to good yields.
View Article and Find Full Text PDFNat Commun
January 2025
Department of Chemical and Biomolecular Engineering, Yonsei University, Seoul, 03722, Republic of Korea.
1,4-Azaborine-based arenes are promising electroluminescent emitters with thermally activated delayed fluorescence (TADF), offering narrow emission spectra and high quantum yields due to a multi-resonance (MR) effect. However, their practical application is constrained by their limited operational stability. This study investigates the degradation mechanism of MR-TADF molecules.
View Article and Find Full Text PDFOrg Lett
January 2025
Institute of Next Generation Matter Transformation, College of Material Sciences Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian 361021, China.
Domino cascade reactions, which can construct multiple bonds in one pot, are efficient methods to synthesize N-heterocycles and other useful skeletons. Herein, we report an expedient synthesis of polysubstituted benzo[][1,5]naphthyridine via Mn(III)-mediated C-C bond cleavage of cyclopropanols. These reactions were initiated by addition of β-carbonyl radicals, generated from cyclopropyl alcohols in the presence of Mn(III), to 2-(2-isocyanophenyl)acetonitriles to give quinolin-3-amines, which went through intramolecular cyclizations and dehydrogenation to give the final products.
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