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4-Cyano-6-methoxyquinolones: Syntheses and Luminescence Properties
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1  Institut für Chemie, Organic Synthesis Group, Karl-Franzens-University of Graz Heinrichstrasse 28, A-8010 Graz, Austria

Abstract: Cyano functionalized 6-methoxyquinolin-2-ones were synthesized from malonic acid derivatives and p-anisidines in multistep reactions via 4-chloro-6-methoxyquinolin-2-ones. Introduction of cyano substituents resulted in 3,4-dicyano-6-methoxyquinolin-2-ones or 4- cyano-6-methoxyquinolin-2-ones, depending on the substituents in position 3 and 1. The study of the fluorescence properties of 3,4-dicyano-6-methoxyquinolone showed emission values up to 550 nm (black curve) combined with large Stoke\'s shifts , whereas 4-cyano-6- methoxyquinolones gave lower values (e.g. blue curve) comparable to earlier findings.