Copper-Catalyzed Tandem Radical Cyclization of 8-Ethynyl-1-naphthyl-amines for the Synthesis of 2 H-Benzo[ e][1,2]thiazine 1,1-Dioxides and its Fluorescence Properties

J Org Chem. 2020 Oct 2;85(19):12526-12534. doi: 10.1021/acs.joc.0c01725. Epub 2020 Sep 16.

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).

Publication types

  • Research Support, Non-U.S. Gov't