2020
DOI: 10.1021/acs.joc.0c01725
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Copper-Catalyzed Tandem Radical Cyclization of 8-Ethynyl-1-naphthyl-amines for the Synthesis of 2H-Benzo[e][1,2]thiazine 1,1-Dioxides and its Fluorescence Properties

Abstract: A copper-catalyzed radical cascade dehydrogenative cyclization of N-tosyl-8-ethynyl-1-naphthylamines under air is described herein for the synthesis of thioazafluoranthenes. The reaction proceeds smoothly with high efficiency and a broad reaction scope. The product is indeed a new fluorophore and its photophysical properties are also investigated. Based on the results, we are pleased to find that the Stokes shift of amino-linked thioazafluoranthenes in dilute tetrahydrofuran is determined to be 143 nm (4830 cm… Show more

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Cited by 12 publications
(3 citation statements)
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“…Arylated benzo­[ b ]­thiophene 1,1-dioxide derivatives were demonstrated as novel organic functional material molecules exhibiting obvious AIE characteristics. , The application of new synthetic methodologies to rapidly and directly construct novel π-conjugated fluorescent core skeletons has been attracting extra attention . Using the Pd­(II)-catalyzed C–H oxidative Suzuki coupling strategy, a series of π-conjugated arylated benzo­[ b ]­thiophene 1,1-dioxides with the AIE effect were synthesized and characterized.…”
Section: Results and Discussionmentioning
confidence: 99%
“…Arylated benzo­[ b ]­thiophene 1,1-dioxide derivatives were demonstrated as novel organic functional material molecules exhibiting obvious AIE characteristics. , The application of new synthetic methodologies to rapidly and directly construct novel π-conjugated fluorescent core skeletons has been attracting extra attention . Using the Pd­(II)-catalyzed C–H oxidative Suzuki coupling strategy, a series of π-conjugated arylated benzo­[ b ]­thiophene 1,1-dioxides with the AIE effect were synthesized and characterized.…”
Section: Results and Discussionmentioning
confidence: 99%
“…Diels–Alder reaction and transition metal-catalyzed reactions are the most commonly used methods for their synthesis. 36–38…”
Section: Introductionmentioning
confidence: 99%
“…Among them, five-, six-, and seven-membered benzosultams are particularly important, and some of them, such as melodica, picrotoxic, and tianeptine, have already been booming in the pharmaceutical market (Figure ). There are a number of approaches available for the synthesis of benzosultams, mainly including intramolecular transition-metal (TM)-catalyzed or stoichiometric hypervalent iodine-mediated C–H amination, intramolecular TM-catalyzed cross-coupling, and intermolecular annulation reactions of aryl sulfonamides with alkynes, alkenes, or other two-carbon synthons . These strategies offer efficient access to benzosultams; however, they more or less suffer from some limitations such as harsh reaction conditions, the use of stoichiometric oxidants, or the use of harmful and expensive TM catalysts.…”
mentioning
confidence: 99%