Synthesis and Properties of Dibenzo[a, j]acridines. Issue 36 (2nd September 2020)

• Record Type: Journal Article
• Authors: Ammon, Erich; Ohlendorf, Lars; Villinger, Alexander; Ehlers, Peter; Langer, Peter
• Is Part Of: European journal of organic chemistry. Issue 36(2020)
• Page Start: 5867
• Page End: 5875
• Publication Date: 2020-09-02
• Subjects: Homogeneous catalysis -- Cross‐coupling -- Cycloisomerization -- Heterocycles -- Palladium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202001002
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A convenient three‐step synthesis of dibenzo[ a, j ]acridines is reported which relies on regioselective Pd‐catalyzed cross‐coupling reactions of 2, 3, 5, 6‐tetrachloropyridine and subsequent Brønsted acid mediated cycloisomerization. Products are obtained in good yields and the method is broadly applicable. For selected dibenzo[ a, j ]acridines, photophysical and electrochemical properties were studied. Abstract : Dibenzo[ a, j ]acridines have been synthesized in three steps and high overall yields using a Brønsted acid mediated cycloisomerization as the final key step. Optical‐ and electrochemical properties have been studied by UV/Vis‐ and fluorescence spectroscopy as well as cyclic voltammetry.