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 −1 ).

Palladium-Catalyzed C2-Selective Direct Arylation of Benzo[b]thiophene 1,1-Dioxides with Arylboronic Acids

“…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.…”

Fluoranthene dyes for the detection of water content in methanol

“…Diels–Alder reaction and transition metal-catalyzed reactions are the most commonly used methods for their synthesis. 36–38…”

Structurally Diverse Synthesis of Five-, Six-, and Seven-Membered Benzosultams through Electrochemical Cyclization

“…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.…”